The Bennington and surrounding areas have a wide diversity of trails through beautiful and varied landscapes - there is something for every level of hiker! Look below to find short descriptions of some of our local trails.

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Bennington, North Bennington, Woodford, Pownal

Bennington, North Bennington, Woodford, Pownal Areas
Bald Mountain (access from Bennington):  7.9 mile out and back trail with 2162 foot elevation gain, rated as moderate. Be sure to stop off at White Rocks about 2/3 of the way up to get a great view of Bennington. White Rocks is a short trail off the main trail - it does not have a sign, but is marked with rock cairns. If you leave a car at both ends, you can combine this with the Bald Mountain Trail ending in Woodford to go completely over the mountain. The trailhead is located in Bennington at 449 North Branch Street where there is parking.
Bald Mountain Trail (access from Woodford): 3.6 mile out and back trail with 1522 foot elevation gain, rated as moderate. The trail winds through beautiful forests, up into the pines and leads to Bald Mountain. If you leave a car at both ends, you can combine this with the Bald Mountain trail ending in Bennington to go completely over the mountain. Parking is on Harbour Road near the large water tank in Woodford. Parking is available on the side with the water storage tank. (The right side is private property)
Bennington Area Trail System (BATS): this is a series of trails within Bennington and on Mt. Anthony. Trails are open for hiking, biking, running, snowshoeing, and cross country skiing. The trails vary in length and difficulty and can be combined to form many different loops. Check the BATS website for much more information. Parking: 1. SVC Campus - check the website for updates on this 2. south end of Camelot Village 66 Colgate Heights, Bennington 3. Southwestern Vermont Medical Center (please don't park in employee lots or in prime spots needed for patients) 100 Hospital Drive, Bennington, 4. Stark Street Playground Stark Street, Bennington ​
Bolles Brook: walk along the beautiful brook on a forest service road. Take Route 9 east of Benninton, turn onto Harbour Road and follow it to the end. There is no parking at the end of the road, but you can park off the side of the road before the last house and property. You can take this trail up to the West Ridge Trail which connects to the Long Trail. 
Bradford-Putnam Wetlands:  Family stroll, short walk amongst ponds reclaimed by Superfund.  Great for young kids to see frogs.  Drive up Burgess Road, watch for signs on right.  May need insect repellent.
Greenberg Headwaters Park:  a 168-acre gem within walking distance from downtown Bennington. Numerous hiking trails criss-cross the property, taking you from a beautiful upland meadow, through hardwood forests, and along the Walloomsac River. Wildlife is abundant throughout the year, so be on the lookout for otter, beaver, muskrat, turtles, and the resident barred owls. You can access Greenberg Headwaters Park from three parking areas on Beech Street, Belvedere Street, and Morgan Street in downtown Bennington. There is a short boardwalk and wetland viewing platform near the Morgan Street entrance, but if you want to hike, park at the Beech Street or Belvedere Street parking areas.
George Aiken Wildflower Trail in the Hadwen Woods: The beautiful Hadwen Woods and George Aiken Wildflower Trail (GAWT) are adjacent to the Bennington Museum. The trail showcases the native wildflowers and ferns that George Aiken loved, propagated, and wrote about in his book, Pioneering with Wildflowers. One-third of a mile long, with a 235 foot mid-section connector trail and a few benches along the way, it beckons visitors to take a moment to relax and enjoy the beauty that is Vermont’s alone. George Hadwen, a long-time Bennington resident and museum trustee, and his wife Marie donated the six-acre Hadwen Woods property to the museum. Volunteers are adding native wildflower and fern gardens to the landscape of indigenous trees and plants along the brook and throughout the paths, woods, and fields. The trail is used as a learning laboratory featuring plant identification markers, printed information about individual plants and other topics of interest to visitors, and educational programming for children and adults. Please be respectful of the surroundings. Leave no litter behind and keep your pets on a leash and pick up after them. The trail is open to the public from dawn to dusk. The Bennington Museum is located at 75 Main Street, Bennington, VT.
Dome Trail: 4.7 mile out and back trail with 1702 elevation gain, rated as moderate. Three mile hike to the peak can be combined with the Agawon Trail to the Broad Brook Trail to form a loop. Limited views at the peak but a beautiful climb along large rock formations near the top. Parking at 379-203 White Oaks Road, Pownal.
Glastenbury Mountain via the Long Trail: 22.4 mile out and back trail with 5400 foot elevation rated as difficult. There is a steep ascent from the trail head, multiple campsites along the way, and a fire tower at the summit. Park at the trailhead off of Route 9 just east of Bennington.
Glastenbury Mountain and West Ridge Loop: 21.8 mile loop trail with 3640 foot elevation gain, rated as difficult. There are few opportunities on Vermont's Long Trail for loop back-packing trips. This hike, through remote forests and over several mountains, is an excellent exception. Your first day, follow the Long Trail and AT north from VT route 9 through an isolated forest to Goddard Shelter and the summit of Glastenbury Mountain. A summit fire tower provides spectacular views of southern Vermont. The second day, you hike south on the West Ridge Trail to the summit of Bald Mountain and then back to VT Route 9. Park at the trailhead off of Route 9 just east of Bennington.
Goddard Shelter via West Ridge Trail: 17.7 mile out and back trail with 4051 foot elevation gain, rated as difficult. The trail follows the Woodford Hollow trail to Bald Mountain, the traverses the West Ridge Trail to the Goddard Shelter. Parking is on Harbour Road near the large water tank in Woodford
Grout Pond: 2.7 mile loop trail around a lake, with 249 foot elevation gain, rated easy. There are also 10 miles of trails that wind around Grout Pond and access the north end of the Somerset Reservoir. Click here for maps and more information. Parking at 207 Grout Pond Road off of Route 100 near Wardsboro, VT.
Harmon Hill via the Long Trail:  a 3.6-mile out-and-back trail with a total elevation gain of 1265 feet, rated moderate to difficult. It’s very steep at the beginning, with lots of rocks and switchbacks. The trail levels out after about a mile, traveling through a lovely meadow. Great views of Bennington and surrounding mountains are obtained by going about 200 feet perpendicular to the trail and out and down a slope from the summit into the clearing.
The trail is located on Route 9 just east of Bennington. Park your car at the Appalachian Trail parking area on the north side of the road, and cross Route 9 to head south.
Little Pond Trail: 4.8 mile out and back trail with 544 foot elevation gain, rated as moderate. The trail follows a wide forest road until the path turns off to Little Pond. (There is also a spur trail that connects to the Long Trail.) Park at the Little Pond Parking lot off of Route 9 in Woodford.
Maple Hill via the Long Trail: 4.9 mile out and back trail with 1361 foot elevation gain, rated as moderate. This hike follows the combined Long Trail and Appalachian Trail northeast from Route 9 in southern Vermont. Park your car at the Appalachian Trail parking area on the north side of the Route 9 just east of Bennington.
Mile Around Woods: 1.3 mile loop trail (opportunities to make this longer) with 137 foot elevation gain, rated as easy. Delightful flat loop of about 2 hours, suitable for families.  Open woods.  many wildflowers in season.  Go north from Bennington on 67A to the center of North Bennington, opposite Powers Market.  Turn left and west onto West St and pass McCullough Mansion.  Limited parking on left at a farm gate.  Enter from here.See more information here. 
Mount Olga: 1.7 mile loop trail with 508 foot elevation with a fire tower at the top, rated easy to moderate. The trail up Mount Olga is located in the Molly Stark State Park which was named after the wife of General John Stark. During the season there is a fee for parking and day use. Camping is allowed as well for a fee. Parking is in the state park at 705 Route 9. There is more information at Molly Stark Park.
Paran-Frost Trail: 3.1 out and back trail (part can be done as a loop) with 255 foot elevation gain and rated as moderate. The trail goes over small bridges, next to a lake and through some forest. There is parking at either end at the Robert Frost Stone House Museum at 121 Route 7A, Shaftsbury or at Paran Lake at Houghton Lane, North Bennington. More information about the Robert Frost Stone House Museum and Paran Lake.
Prospect Mountain: Prospect Mountain maintains more than 30 kilometers of trails. When the snow falls, the trails are expertly groomed for both skating and classical cross-country skiing. Most trails have tracks set on either side with a wide skating lane in the center. There are also special snowshoeing and single-track trails. We have trails from beginner to expert. More Information for Prospect Mountain. 
Somerset Road: (Forest Road 71) connects with Kelley Stand Road, and offers nearly 9 miles of scenic driving following the East Branch of the Deerfield River, with roadside campsites along it's length. Great for bicycling. There are numerous hiking, and snowmobiling trails off of this road.
Stratton Mountain : 9 mile loop trail with 1910 foot elevation gain, rated as moderate to difficult. this long, beautiful hike has several scenic overlooks of Somerset Reservoir and Stratton Pond as well as nice views from the summit fire tower. You can also hike out and bak the same trail in 6.8 miles for a shorter trip. Take VT 100 to the junction of Arlington-West Wardsboro Road (or Kelly Stand Road) in West Wardsboro. Drive 7.1 miles west on Arlington-West Wardsboro Road to the LT?AT parking lot on the north side of the road.
Stratton Pond: 7.8 mile out and back trail with 660 foot elevation gain, rated moderate. This long but almost level hike leads to Stratton Pond, which is located in the 15,680-acre Lye Brook Wilderness. Several lakes, streams and bogs dot the landscape. The wilderness area contains beautiful waterfalls and meadow, as well as the remnants of old logging railroads and sawmills. The trail is located on the north side of the Arlington-West Wardsboro Road (also known as Kelly Stand Road). From VT 100 in West Wardsboro drive 8.2 miles west of the Arlington-West Wardsboror Road to the the intersection of USFS Road FR71.There is a parking lot of FR 71 just east of the intersection.
Woodford Trail: 2.4 mile loop trail, 219 foot elevation gain, around the Adams Reservoir in the Woodford State Park. A lovely trail with lake and forest views. More information about Woodford State Park. There is swimming and canoeing (rentals available) in small lake, also picnicking and camping. In season parking is in the state park located at 142 State Park Road off of Route 9, Bennington, there is a fee. Out of season parking is across Route 9 in the snow mobile lot, no fee.
Williamstown, North Adams, Adams

Williamstown, North Adams, Adams Areas
Ashuwillticook Rail Trail: The Ashuwillticook Rail Trail is an old railroad track converted into a 10-foot wide paved trail. The trail runs 11.2 miles through the towns of Cheshire, Lanesborough and Adams. Cheshire Reservoir, and the Hoosic River offer outstanding views of the scenery and wildlife. Parking lots and restrooms are available at selected locations along the way. The trail is used for biking, running, walking and cross country skiing. More information here.
Berkshire Natural Resources Council: for detailed descriptions and downloadable maps of all 55 properties across Berkshire County visit bnrc.org
Berlin Mountain: 5.4 mile out and back trail, 1263 foot elevation gain rated as moderate. The trail is easy to follow and ends with a clearing and view at the top. It starts at the Petersburg Pass parking lot on Route 2 in NY, look for the kiosk to start the hike.
Chestnut Trail to the Class of '98 Trail to the Appalachian Trail: 3.0 mile out and back trail with 1295 foot elevation gain. Park along the side of the road at 144 Chestnut St, Williamstown, MA.
Hopkins Memorial Forest: The HMF contains about 15 miles of trails open to the public for walking, skiing and snowshoeing. Horseback riding is allowed only on the Ford Glen Brook and Carriage Road trails. All wheeled and motorized vehicles, including bicycles, are prohibited in the HMF.
You can go further up the Birch Brook trail to the Taconic Crest. When you reach the Taconic crest you can go South to the Petersburg pass on Highway 2 or go North about a mile or so to the Snow Hole for a more rigorous hike.  (Some people take 2 cars and spot one at either end of the hike so that they can make a one way hike). The Snow Hole is a natural rift in the geology and easy to walk down into. We have uncovered snow hiding under leaves at the bottom of the Snow Hole in September from last year’s snow fall. It is so cold down there. If you are on the Taconic Crest, the Snow Hole is a MUST!
     Birch Brook Trail. The BBT leaves the Upper Loop Trail near a bridge across the North Branch of Birch Brook. The trail climbs the steep, east-facing slope of the Taconic Range, crossing the New York state border at 1.1 miles and reaching the Taconic Crest Trail 1.5 miles from the Loop Trail.
     Carriage Road Trail. The CRT (1.4 mile), also known as the Horse Trail, follows the alignment of the Buxton Farm carriage road running between the Rosenburg Center at the eastern HMF entrance and the northern reaches of NW Hill Road.
     Ford Glen Brook Trail. The FGBT parallels Ford Glen Brook between the Hoosic River and Northwest Hill Road. The eastern half of this 0.6 mile-long trail is on private property.
     Hoosic River Tail. The mile-long HRT parallels the Hoosic River along the eastern boundary of the HMF. The HRT starts at the old Boy’s Club Camp field on the FGT and ends at the northeastern corner of the Forest.
     Logging Roads. A network of logging roads in the VT section of the HMF connects Northwest Hill Road and the Taconic Crest Trail. Caution should be used when using these roads since it is easy to become confused about which trail you are on.
     Lower Loop Trail. The LL forms a loop of about 1.5 miles immediately west of the Rosenburg Center at the main entrance to the HMF. The northern leg of the trail is on the old carriage road, while the southern leg parallels an old farm road and has a fairly steep section just west of the Moon Barn.
     Upper Loop Trail. The 2.6 mile UL is the western loop of a figure-eight formed with the LL. The trail cross rolling terrain and can be hiked in less than two hours.
     Nature Trail. The NT, approximately 0.75 miles in length, starts just north of the Rosenburg Center. It passes through the old sugar bush and then into a second-growth forest that originated in 1935 when the Forest Service realigned the Carriage Road. The NT extends to an even-aged red oak stand before looping back along the Carriage Road Trail to the Rosenburg Center.
     Shepherd’s Well Trail. The SWT (1.0 mile) connects the Taconic Crest Trail with the western upper reaches of the RRR Brooks Trail (that ends on Bee Hill Road at Flora Glen in Williamstown).
Fitch Trail to RRR Brooks Trail: 4.2 mile loop trail, 1082 foot elevation gain located near Williamstown, Mass. rated as moderate. Parking is on Bee Hill Road off of Route 2.
Mahican-Mohawk Trail to Indiana Trail Loop: 4.7 mile loop trail, 1164 foot elevation gain rated as moderate. Part of this trail is quite steep and can be slippery in Winter or with wet leaves in Fall. Parking is at the Mohawk Trail State Forest (fee during open season May -mid October.) More information here.
Mountain Meadow Preserve: 4.3 mile loop trail with 646 foot elevation gain. Although modest in size, the 180-acre reservation rises in elevation from 690 feet at the Williamstown parking lot to more than 1,100 feet across much of the preserve’s Vermont landscape. From the broad meadow a few hundred yards beyond the parking lot, enjoy a view of the Hoosac Valley that includes both Williamstown church spires and Mount Greylock. Climb a half-mile loop trail to a hilltop, from where you can also continue your hike into the Pownal, Vermont side of the reservation. If you prefer your vistas without the uphill walk, enter the reservation from the Pownal parking lot. Massachusetts parking lot on Mason Road off of Route 7. Vermont parking lot on Benedict Road in Pownal, VT. More information here.
Phelps Trail: 4.3 mile loop trail, 1423 foot elevation gain. This loop starts on the Phelps Trail on Oblong Road and goes up to the Taconic Crest Trail, then follow the crest trail for .9 miles until taking the Mills Hollow trail back down to Oblong Road, then walk a short distance along the road to return to the starting point. There is parking at the Phelps trailhead on Oblong Road in Mass. If a longer hike is desired, once reaching the Taconic Crest Trail you could continue up to Berlin Mountain, then retrace your steps back to the intersection of the Crest trail and Phelps trail and continue with the remainder of the hike as written above. This would make about a 7.8 mile hike.
Pine Cobble Trail: 3.3 out and back trail near Williamstown, Mass, 1200 foot elevation gain. There is a nice rocky summit overlooking Williamstown. There is room for about 6 cars on Pine Cobble Road with additional parking off the roadway.
Taconic Crest Trail: a 35.6 mile trail through the Taconic range. It extends from US Route 20 inHancock, Mass to NY Route 346 near the Vermont border. The trail is a mixed old-hickory forest and northern hardwood forest with microclimate summit balds, alkaline loving plant communities and red spruce/balsam fir stands on the higher summits. The trail is marked with blue squares containing white blazes. The entire trail is open to hiking, backpacking, snowshoeing, cross-country skiing, backcountry skiing, and many sections permit mountain biking, horseback riding and snowmobiling as well. Overnight camping is allowed on the trail and a seasonal campground with facilities is located at Berry Pond. Many sections of the trail can be done as day hikes.
Williamstown Rural Lands Foundation Interactive Trail Map - great way to find out additional information about the above trails and more. 
Mount Greylock

Mount Greylock
Mount Greylock State Reservation: There are MANY trails in the Mount Greylock area. Click here to get a downloadable map of the trails. The map shows both summer use and winter use trails.
Bellows Pipe Loop Trail​: 13.6 mile loop trail located near North Adams, Massachusetts, 4721 foot elevation gain rated as difficult. Parking at 423 Pattison Road in North Adams, Mass.
Bernard Farm Trail: 3.7 mile out and back trail located near North Adams, Massachusetts, 1217 foot elevation gain rated as moderate. This is a woodsy hike with well marked blue blazes until the AT, which is white. Easy to follow even when blazes aren't visible. There's an old plane crash wreckage on the left side of the trail about 80% way up. After intersecting the AT, head to the summit of Mt. Greylock which was not much more than a 2.4 mile stroll until the last little bit which is quite steep, but not treacherous. Good views in places. Come in Notch Rd. in North Adams and park in the large Notch Rd. Parking area. You can also enter on the Rockwell Rd side by the Visitor Center and drive up the mountain and back down Notch Rd. You'll see the left turn for Notch Rd. prior to the Greylcok Summit.
The Hopper Trail: 4.8 mile loop trail, 1312 foot elevation gain, rated as moderate. The Hopper Trail begins on Hopper Rd. in Williamstown, MA and climbs gradually and at times very steeply through old forest growth to Sperry Rd and then up to the Mt. Greylock Summit. The Hopper Trail is approximately 2.4 mi from Hopper Rd trailhead to Sperry Road and then an additional 1.7 mi to the Summit. You will need to walk a short distance along Sperry Road to transition from the lower Hopper to the upper Hopper that takes you to the summit. Parking at 1033 Hopper Road in Williamstown, Mass.
Sperry Road to Stony Ledge:​ 1.9 mile out and back trail, 239 foot elevation gain, rated easy. Follow a gravel road through the camping area at Mt. Greylock to the scenic vista of Stony Ledge which offers beautiful views of Mt. Greylock and other mountains. Parking at Sperry Road in Williamstown, Mass.
New York

New York
Dickinson Hill Fire Tower: 2.6 mile out and back trail with 334 foot elevation gain, rated as easy. Just east of Grafton Lakes State Park is Dickinson Hill Fire Tower.  Built in 1924 to monitor forest fires in order to protect Tomhannock Reservoir. Over the years the fire tower was neglected until the Friends of Grafton Lakes State Park agreed in 2010 to carry out the necessary work to restore the Tower so that it can be a permanent and publicly accessible feature of the state park. In May 2011 the restoration of the fire tower began and the Dickinson Hill Fire Tower officially reopened to the public on June 25, 2012. Park in the parking area along seasonal dirt North Long Pond Road just north of where the rough Fire Tower Road reaches the road.You can either walk back down North Long Pond Road from the parking area or head toward Long Pond Trail, turn left and then another left on the Fire Tower Connector Trail.  Then it's straight up the rough section of Fire Tower Road for 1.2 miles before reaching the service road gate on your right. Then it's a final 750 feet up the service road to the fire tower. It's only a 257 foot elevation gain from North Long Pond Road, making this a pretty simple hike. There is a picnic table in the clearing near the tower. There are no views without climbing the sixty foot fire tower. The cabin of the tower provides a spectacular view including the Adirondack Mountains, the Green Mountains of Vermont, the Taconic Range that forms the border between New York and Massachusetts to the east and the Helderberg Mountains to the south and west. Look below for a few pictures and the trail map to Dickinson Hill Fire Tower as well as Grafton Lakes State Park.
Tibbits State Forest: There are approximately 1.6 miles of trail on the north side of Route 7 and 6.3 miles on the south side.oday, New York Route 7 divides the Forest into two sections. There are about four miles of hiking and logging trails. An old logging road starts gradually up the hill from the parking spot on Route 7. To the left is the "Nature Trail" and to the right a two mile hike around the back side of the hill following another logging road.  If you head west from the start of the "Nature Trail", you will find easy walking for about 1.6 miles as it parallels Route 7 and Shingle Hollow Creek. The forest has groves of pine, hemlock, and white oak. Ferns and wildflowers thrive throughout. For those outdoor enthusiasts, the trails lend themselves to hiking and cross-country skiing along with trail rides. Click here for a map of the region.
Savoy State Forest

Savoy State Forest
Busby Trail to Spruce Hill: 3 mile out and back trail with 680 foot elevation gain, rated as moderate. The trailhead is located 3 miles from MA Route 2, at the intersection of Central Shaft Road and Old Florida Road (a rocky dirt road), just beyond the state forest headquarters at 260 Central Shaft Road, where you may also pick up a Savoy Mountain State Forest Trail Map. Park on the shoulder of Old Florida Road. Buy leaving a car at each end, you can combine this with the Hoosac Range trail to make an up to Spruce Hill and over the other side. Click here for more information.
Hoosac Range Trail to Spruce Hill: 6.2 mile out and back trail with 938 foot elevation gain, rated as moderate. Access to Spruce Hill is on Route 2 in North Adams east of the hairpin turn.  There is a convenient parking area on the south side of the road just west of the Florida, Massachusetts border.  This is a popular hiking destination due to the fact that there are several breathtaking views in many different directions along the ridge within a relatively short distance and because the hike is not particularly difficult.  The trails in along the ridge are well maintained and are very easy to follow.  From this area, you will see Mt. Greylock, the Taconic Range on the New York border, The Dome in Vermont and possibly some other surprises on a clear day. Parking in a lot at 2350 Mohawk Trail, North Adams, MA.
Tannery Falls: 4.8 mile loop trail with 620 foot elevation gain rated as moderate. The trail features a beautiful waterfall. Park in a lot at Burnett Rd, Savoy, MA.

​Savoy State Forest: This state forest offers many hiking trails for all levels of difficulty in both summer and winter use.  Click here for a map of the Savoy State Forest Trails.
Arlington, Manchester and North

Arlington, Manchester and North
Bromley Mountain via Long Trail (AT): 5.3 mile out and back trail with 1414 foot elevation gain, rated as moderate. The trail, part of the Appalachian/Long Trail system, is identified by white trail blazes.  This trail follows a rocky course through a mixed northern hardwood forest.  At the east end of the parking area, opposite the entrance, follow the trail along the road for about 50 feet then take a sharp left turn which leads over a narrow bridge. From this point the trail follows Bromley Brook.  At 0.9 mile the trail crosses over Corridor 7, a major snowmobile route.  After 1.6 miles, the trail makes a couple of sharp turns and becomes steeper. At 2.3 miles, there is a spur trail leading to the Bromley Shelter and tenting area.  As the trail nears the summit, it opens onto Bromley Mountain’s “Run Around” ski trail.   Follow this to the top where you will see an AT/LT sign, Summit Ski Patrol Station, and an observation deck.  From the summit there are excellent views in all directions.  In particular, Stratton Mountain is to the south and Mount Equinox is to the west. Directions from Manchester Depot, VT: Five miles east of Manchester Depot on SR 11 / 30 is a parking area and trail access for the Appalachian / Long Trail. Begin there.
Green Mountain Trail: 9 mile out and back trail with 2200 foot elevation gain, rated difficult. From Route 7, turn east at Danby onto Forest Road 10. Park at the Big Branch Picnic Area on Forest Road 10. The trail begins about 100 feet west of the picnic area, on the road. Hike north on the blue blazed trail for 4.1 miles to Little Rock Pond. for a loop route follow the white blazed Long Trail (AT) 2.0 miles south back to Forest Road 10. Turn right (west) for a 0.5 mile walk back to the Big Branch Picnic Area. Total loop is 6+ miles rated as moderate. Directions from Danby, VT: Take US 7 turning east on Forest Road 10. Park at the Big Branch Picnic Area. Trail begins about 100 feet west.
Griffith Lake/ Baker Peak: 6.6 mile out and back trail, rated moderate to difficult. 2 miles north of Emerald Lake, on route 7, go east on South End Road to the trailhead parking area. Follow the blue blazed trail 2.0 miles to the McGinn Brook crossing. The trail divides. to the left it is 0.8 miles to the summit of Baker Peak, which offers views of the Otter Creek Valley, Dorset Peak, and other peaks in the Taconic Mountain Range. To the right, it is 1.3 mils to Griffith Lake. You can make this a loop trail by combining a section of the Long Trail (LT/AT) to make a 7.7 mile loop, 2109 foot elevation gain.
Haystack Mountain: 3.1 mile out and back trail with 1167 foot elevation gain, near Pawlet, Vt, rated as moderate. Generations of Pawlet families – and visitors from around the world – have climbed the steep slopes to the top of Haystack Mountain to take in the spectacular 360-degree views of Bald and Middle Mountains, the north-south forested hills and the serene Mettowee Valley. This preserve features a series of rounded, forested peaks in the northern Taconic Mountains, clustered in an extensive landscape of unbroken forest. Locals call Haystack, Middle and Bald Mountains the Three Sisters. Warm southern aspect and shallow soils produce drought-like conditions on the hills and promote the growth of several unusual natural communities, including dry oak woodlands and dry oak-hickory-hophornbeam forests. Turkeys, grouse and bobcats roam the rocky landscape. Peregrine falcons sometimes nest on the cliffs of Haystack. These forested hills also provide nesting habitat for neotropical migrant songbirds that rely on unfragmented forest blocks. Parking is only on the side of the road at 1171 Waite Hill Rd, Pawlet, VT.
Homer Stone Brook Trail: 5 mile out and back trail with about 1200 foot elevation gain, rated as moderate to difficult. From South Wallingford, take the Hartsboro Road to the Home Stone Road. The trail is the first left on an old road which follows Home Stone Brook for 2 miles. The trail then bears right and uphill for 0.5 miles to Little Rock Pond and the AT/LT. 
Keewaydin Trail: 3.4 mile out and back trail with 1210 foot elevation gain, rated as moderate. From the upper end of the white Rocks Picnic Area near Wallingford, follow the blue blazes 0.4 miles to Bully Brook Waterfalls and 0.8 miles to the AT/LT. Directions from Wallingford, VT: Travel SR 140 east to the White Rocks Picnic Area. Trail may be accessed there.
Little Rock Pond: 4 mile out and back trail rated easy. From Route 7 in Danby, turn east onto Brooklyn Road, Forest Road 10. Park at the AT/LT crossing. Follow the AT/LT north 2 miles to Little Rock Pond.
Little Rock Pond and Green Mountain Trail: 6.5 mile loop rated as moderate. The Green Mountain Connector Trail begins across the road from the parking area and heads west for 0.6 miles to the Green Mountain Trail. Hike north on the blue blazed trail for 3.9 miles to Little Rock Pond. Several vistas on the Green Mountain trail provide views of the pond and surrounding area. Follow the AT/LT south for 2.0 miles back to the parking area. From Route 7 in Danby, turn east onto Brooklyn Road, Forest Road 10. Park at the AT/LT crossing.
Lye Brook Falls: 4.7 mile out and back trail with 938 foot elevation gain, rated as moderate. Lye Brook Falls is a steep and impressive seasonal waterfall that demands a springtime visit or see it frozen in the winter. These falls, which are estimated to be 125 feet and were once called Trestle Cascade, drop in a series of what seems like hundreds of mini-steps over six or seven major tiers. The trail, marked with blue blazes, follows the Lye Brook Trail for just under 2 miles. At around the 1.8 miles, there is a spur trail to the right that leads to the falls. There will be a sign, though some have reported it can be misleading. Climbing around the falls is not recommended, as wet rocks can be very slippery. Parking is on Glen Road, Manchester Center, Vt.
Mount Equinox and Lookout Rock: 6.3 mile out and back trail with 2883 foot elevation gain, rated as difficult. Being the highest mountain in the Taconic Range, the climb to the top of Equinox Mountain is steep and unrelenting. At the summit, you'll find a visitor's center and a monastery that can also be accessed by car. Lookout Rock is another two tenths of a mile from the summit, which has views of nearby Manchester Village, as well as a unique and beautiful marble bench. More information here.  Park at 53 Seminary Ave, Manchester Center.
Prospect Rock Trail: 3.1 mile out and back trail with 1010 foot elevation gain, rated as moderate. The trail, blazed with blue, follows the old Rootville Road up along the Downer Glen Ravine.  After passing the Forest boundary, the trail gets steeper and crisscrosses several mountain streams.  At 0.8 miles the trail leaves the brook at an old spring.  The trail then meets up with the Appalachian/Long Trail at about 1.7 miles (same road).  Just past the junction, a spur trail on the right leads 200 feet west to Prospect Rock.  The summit has a fine view of the Manchester Valley.  To the west is the prominent Mount Equinox, the tallest mountain in the Taconic Range.  The lesser peaks of Little Equinox, just south of Mount Equinox, and Mother Myrick Mountain to the northwest are also visible. Directions from Manchester Depot, VT: Travel northeast on SRs 11 / 30 making a sharp right onto East Manchester Road. Make an immediate left onto Rootville Road. Follow until the road forks (which is practically the end of the road) and bear right. Trailhead is at the end. Parking is limited.
Spruce Peak: 4.8 mile out and back trail, rated as moderate. From the parking area, cross the highway and hike south on the AT/LT for 2.4 miles to Spruce Peak. A short spur trail leads to the summit, which affords views of the Manchester Valley and the Taconic Mountain Range. Five miles east of Manchester Center, on Routes 11 & 30, is a parking area for the AT/LT.
Styles Peak and Peru Peak Loop: 10.9 mile loop trail with 1788 foot elevation gain, rated as difficult. From the Mad Tom Notch trailhead on Forest Road 21, follow the AT/LT north 1.6 miles to Styles Peak, where there are partial views. Continue another 1.7 miles to reach Peru Peak, where a spur trail leads to an overgrown vista. Peru Peak shelter is another 1.3 miles north and Griffith Lake is 0.8 miles past the shelter. On the north side of the lake, the trail meets an old carriage road and heads south 2.0 miles to the end of FR 58. Follow FR 58 south about 3.0 miles to the junction with FR 21. The parking area is 0.5 miles to the east.
White Rocks Ice Bed Trail: 3 mile out and back trail with 429 foot elevation gain rated as easy to moderate. From the White Rocks Picnic area, follow the trail for 0.2 miles to a good view of the White Rocks. To follow the Ice Bed Trail, bear to the right at the fork in the trail. The distance from the fork to the ice beds is 0.6 miles. Directions from Wallingford, VT: Travel SR 140 east to the White Rocks Picnic Area. Trail may be accessed there.
Wilmington, Brattleboro

Wilmington, Brattleboro
Haystack Mountain Trail: 4 mile out and back trail with 1026 foot elevation gain, rated as moderate. The trail, marked with blue blazes, follows an old gated road on a steady moderate incline to Binney Brook ravine.  Turning southwest (left) at about 0.5 miles, the trail then begins to climb steeply to the west ridge of Haystack Mountain.  This section of trail is mainly a snowmobile trail, so look for and follow the orange snowmobile signs.  The trail makes a few turns leading through different forest types until reaching the summit trail junction.  Turn right and follow the blue blazes again, making a few more turns until the trail reaches the summit. From the partially wooded summit some views include Haystack Pond and Mt. Pisgah (Mt. Snow) to the north, Harriman Reservoir to the south, and large windmills to the southwest.  The summit, from different locations, also has many great views of bordering mountains. Parking is along the roadside at 4 Upper Dam Rd, Wilmington, VT. Click here for more information.
Hogback Mountain: 2.7 mile loop trail with 360 foot elevation gain, rated as easy. Hogback offers a wealth of natural and scenic resources including the headwaters of the Green River watershed.  It provides important wildlife habitat for a variety of mammals such as deer, porcupine, bobcat, black bear and moose. It also includes summer habitat for neotropical migrant birds such as the black-throated blue and black-throated green warblers. Hogback Mountain is open year-round to the public for hiking, snow-shoeing and other low-impact recreation. More information here. Parking at a large lot at 7788 VT-9, Brattleboro, VT.
The Pinnacle via J. Latham Trail: 4.3 mile out and back trail with 708 foot elevation gain, rated as moderate. The Pinnacle is the highest and most scenic peak (+/-1683 feet) in Westminster, Vermont. It is located on the Windmill Ridge, straddling the Brookline/Westminster line. The view from the Pinnacle overlooks Hedgehog Gulf in Brookline and westward to Mount Snow and Stratton Mountain, over 20 miles away. Parking at 1937 Old Athens Rd, Putney, VT.
Putney Mountain: 1.2 mile hike with 157 foot elevation gain rated as easy. Short, easy hike to nice views. Hawks in abundance during migration season. A short hike that is good for families, as it's not too hard. Bird lovers will enjoy the spring and fall hawk migration seasons. From parking take the white blazed Ridgeline Trail to the summit. It follows a well defined woods road. Return this way or bear left on a short blue blazed trail then turn left (south) onto the yellow blazed trail and take it back to your car.
The Valley Trail: The Valley Trail connects the resort villages of Wilmington and Dover in southern Vermont. The southern end of the trail is located off Route 9 in Wilmington across from Reardon’s Crossing Bridge, while the northern end terminates at Mount Snow in Dover. Nine trailheads and parking areas along the way and several spurs off the main trail enable users to hike or bike all or part of the trail. Click here to see a map of the trail.
Wilmington Walking and Hiking Trails: Click here to see descriptions of 9 walking and hiking trails in the Wilmington area.
In addition to section hiking or thru-hiking, you can create a day hike from many of the sections of the Long Trail.
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Long Trail/Appalachian Trail:  The Long Trail, America's oldest long distance trail, is a 272 mile footpath that follows the spine of the Green Mountains from the Vermont/Massachusetts border to Canada. The Appalachian Trail coincides with the Long Trail from the Massachusetts border to Maine Junction at Willard Gap just north of U.S. 4. There are 166 miles of side trails which make for great day hikes.

For more information check these sites:
 Long Trail information 
or
​GMC Long Trail
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