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Berkshires and Pioneer Valley have lovely & mountainous places to walk

Summer Family Hike - Jiminy Peak Mountain Resort - Hancock, MA
Jiminy Peak Mountain Resort

37 Corey Road -- Route 43 Hancock, MA, 01237 Phone: 413-738-5500 Toll-Free: 800-882-8859

Hike up to a mountain summit or walk a trail network: two great options at full-service resort

Nothing gives you a better workout in the great outdoors than hiking, unless it’s hiking up a mountain! At the Jiminy Peak Mountain Resort, you can hike up the 2,380-foot mountain to the summit, where your reward, in addition to knocking off all those calories, will be astonishing views of the Berkshire Mountains. For those who want something a little less strenuous, there’s the walking trail network near the western border of the 167-acre property. You can get a trail map at the front desk of the Country Inn, at the ticket window in Crane Lodge or at the welcome center customer service desk. After your hike, grab lunch or dinner at John Harvard’s Restaurant & Brewery in the inn or at Christiansen’s Tavern.
Forest Hiking - Adventure East - Sunderland, MA
Adventure East

11 Bridge Street Sunderland, MA, 01375 Phone: 413-800-5345

Get moving! Adventure center offers a variety of walks, hikes to connect you with the great outdoors

Want to go for a walk? Whether you prefer a gentle stroll through the woods or a hike through more challenging terrain, you can find your walk at Adventure East, where they are dedicated to connecting you with the great outdoors. And that means walking and hiking adventure all year long on peaceful trails with iconic views. In the winter, there are walks (some with snowshoes and shoe spikes) where you’ll look for signs from area wildlife and how to identify different trees. In the spring, go into the woodlands and learn how to forage. Summer and fall mean old-growth forest walks, photograph workshops, hunting for mushrooms. Forest-bathing walks include a rejuvenating stroll through the forest with a guided meditation, gentle movements and breathing exercises.
mclennen reservation
McLennan Reservation

Fern Road Tyringham, MA Phone: 413-298-3239

Hiking, birding, picnicking

From the entrance of the McLennan Reservation, a 1.5-mile trail follows the graceful rises and dips of this densely forested landscape before reaching the high plateau where Hale Swamp (created when beavers dammed Camp Brook long ago) is located. Round Mountain and its neighbor, Long Mountain, form the backdrop for the reservation, which was once part of the Ashintully estate, whose gardens are located at the southern end of the valley.
mount everett state reservation
Mount Everett State Reservation

143 East Street Mount Washington, MA Phone: 413-528-0330

Good for scenery and vista-viewing; free access; pets permitted.

Mount Everett is close to the juncture of Connecticut, Massachusetts, and New York State. The hike up to its 2,624-foot summit is challenging, but the reward is views that are out of this world. The summit road is supposed to be open in the summer; it is wise to call ahead to make sure the road will be open. If the summit road is open, you can drive to the top. Directions.
Here’s a tip from BerkshireHiking.com: If you are looking for a hike that is a workout but not too grueling, park at the base of the Everett's summit road (East Street in Mount Washington, MA). Follow the summit road to Guilder Pond, which offers a loop trail. From Guilder Pond you can proceed to white blazes that indicated you’re on the Appalachian Trail. Hop on the A.T. and head for the summit, just a mile away. Map.
Season & Hours: The park is open year-round, sunrise to sunset year-round. Summit road is open in the summer.
Mountain Meadow Preserve

Mason Street Williamstown, MA Phone: 413-458-3144

Mountain Meadow Preserve protects forest, fields, and wetlands along the Massachusetts-Vermont border that are home to bears, coyotes, bobcats, fox, and deer, butterflies, amphibians. There are four miles of easy-to-moderate trails on roads and footpaths, One trail cuts through a spectacular upland wildflower meadow. A second loop trail leads to a summit with views of Mount Greylock and the Taconic Range. The property is owned and managed by Trustees of Reservations
Hours: Open year-round, daily, sunrise to sunset. Allow a minimum of 1 hour. Map.
Metacomet-Monadnock Trail from Holland Glen to Mount Lincoln

This is a 10-mile section of the 117-mile Metacomet-Monadnock Trail (M+M) which is managed the Appalchian Mountain Club. In its entirely, the trail traverses the Metacomet Ridge of the Pioneer Valley region of Massachusetts and the central uplands of Massachusetts and southern New Hampshire.
This 10-mile section is moderately difficult. It takes walkers over ridges and along streams on footpaths and old-town roads, overgrown with mixed forest. Holland Glen, the start of the hike, is a steep ravine laced with a clear stream and shaded by a mature hemlock stand. There’s a waterfall at the top of the glen. Follow the white blazes.
Directions: From Massachusets Route 2, take Route 202 to Belchertown. Take the exit for Route 9 west. Proceed 2.8 miles to parking on the right. The trailhead is just north of parking lot.
Mahanna Cobble Trail

former Bousquet ski area, 101 Dan Fox Drive Pittsfield, MA Phone:

Berkshire Natural Resources Council and Mill Town have developed a permanent trailhead from the former Bousquet ski area. Mahanna Cobble Trail is 2.8 miles round trip and is rated difficult because of elevation changes. “Cobble” is a local term to describe a geologic formation of exposed bedrock high on a ridge.
Directions: Park to the far left of the former Bosquet lodge. Signs direct hikers to a temporary access route from the Bousquet base lodge and parking area, up a ski hill, toward the new Mahanna Cobble trail. Take the beginner ski slope, Drifter, up for 0.4 miles to the start of the trail. After that, the trail is a one mile of abrupt turns and stone steps. There is a spectacular view and stone bench at the apex.
Trail map and guide.
Monument Mountain

Route 7 Great Barrington, MA Phone: 413-298-3239

For almost two centuries, Monument Mountain has been a source of inspiration to poets, novelists, and painters. The summit offers panoramic views of Southern Berkshire County, and three miles of trails lead through a white pine and oak forest. During William Cullen Bryant's stay in Great Barrington, he penned the lyrical poem "Monument Mountain," and on August 5, 1850, Nathaniel Hawthorne and Herman Melville enjoyed a well-chronicled picnic hike up Monument Mountain. A thunderstorm forced them to seek refuge in a cave where a vigorous discussion ensued, inspiring ideas for Melville's new book, Moby Dick.
Hiking Trail - Clarksburg State Park - Clarksburg, MA - Photo Credit Cheryl Bonner
Clarksburg State Park

1199 Middle Road Clarksburg, MA, 01247 Phone: 413-664-8345

Hike 9.5 miles of foot trails surrounding Mauserts Pond. Five winding, looping walking trails offer various difficulty levels, depending on how far you plan to hike. - Trail Map (PDF)
Jug End State Reservation - Egremont, MA - Photo Credit Ben Nickley
Jug End State Reservation

Jug End Road Egremont, MA, 01258 Phone: 413-528-0330

Jug End offers one of the most scenic areas in the Berkshires. The Jug End Loop Trail is a two-mile walk through open fields and hardwood woodlands. This walk also provides access to and parking for the Appalachian Trail. Open year-round, sunrise to sunset. Parking is only for daytime use of the park. No charge to enter the property. Pets are permitted on a 10-foot leash. Off-road vehicles and alcoholic beverages are not allowed.
Warning!: Black bears live here - NEVER confront or feed or tease the bears. Be sure to seal your food and collect all trash to take with you. Rattlesnakes also live in the park. Stay clear of them. - Trail Map (PDF)
Chesterfield Gorge

River Road Chesterfield, MA, 01012 Phone: 413-532-1631

The magnificent gorge, formed by the movement of the Westfield River, offers an easy, one-half-mile path with great views, and another, seven-mile path that is popular with both walkers and mountain bikers. See a full description on our Walking & Hiking page.
Winter Trail - Savoy Mountain State Forest - Florida, MA - Photo Credit Marylea Lueth
Savoy Mountain State Forest

260 Central Shaft Road Florida, MA, 01247 Phone: 413-663-8469

No matter the season, you can go hiking on more than 50 miles of trails at Savoy Mountain State Forest. Experience natural spectacles like rich fall foliage and hawk migration. Spruce Hill on the Busby Trail is recommended by locals for its stunning view. - Trail Map (PDF)
Housatonic River Walk

Dresser Avenue and River Street Great Barrington, MA Phone:

Housatonic River Walk is a paved path that ambles alongside the Housatonic River in Great Barrington, following the Housatonic River between Cottage Street and Bridge Street. It passes the W.E.B. Du Bois River Park. The trail’s two sections are linked by Dresser Avenue and River Street. The upstream section extends from the River Walk bulletin board at 195 Main Street to the William Stanley Overlook. The trail exits at the stairs to St. Peter’s Church parking lot on Dresser Avenue. The downstream section of the trail begins adjacent to the Berkshire Corporation parking lot on River Street and ends at Bridge Street.
Kenneth Dubuque Memorial State Forest - Hawley, MA
Kenneth Dubuque Memorial State Forest

MA Route 8A Hawley, MA, 01339 Phone: 413-339-5504

This 7,882-acre northern hardwood and spruce-fir forest offers 35 miles of mixed-use trails, six miles of hiking trails and one mile interpretive trail around Hallockville Pond. There are many historic sites, such as evidence of an abandoned village; a beehive charcoal kiln; and the remnants of mill businesses. Open: year-round, sunrise to sunset. Access is free. Interior roads are in poor condition. Carry-in, carry-out all your belongings and trash. Snowmobiling is available on 35 miles of trails, conditions permitting. Parking is available at King Corner garage on Route 8A. Prohibited: All-terrain vehicles and alcoholic beverages. - Trail Map (PDF)
Trails - Pleasant Valley Wildlife Sancturary - Lenox, MA - Photo Credit Massachusetts Audubon Society
Mass Audubon’s Pleasant Valley Wildlife Sanctuary

472 West Mountain Road Lenox, MA, 01240 Phone: 413-637-0320

Come and enjoy walking seven miles of trails with access to Lenox Mountain summit. Universally accessible trail (0.3 miles) and boardwalk overlooking Pike’s Pond and an active beaver colony. Summer camp and canoe trips offered on the Housatonic River. - Trail Info and Map
Hours: Open year-round. Trails are open dawn to dusk.
Norcross Wildlife Foundation - Wales, MA
Norcross Wildlife Foundation

30 Peck Road Wales, MA, 01081 Phone: 413-245-1264

There are two miles of marked walking trails through a variety of habitats and wildflower gardens at this 8,000-acre nature preserve and nature education property.
Hours: Trails are generally open April through November, trail conditions permitting. Call ahead during the winter months.
Race Brook Falls

Off Route 41 Sheffield, MA Phone:

This hike includes a beautiful, three-tiered waterfall, which spans most of the hike. The walk starts through a dense pine forest but quickly opens to a young forest. At the top of the waterall is a natural swimming hole. This hike starts right off Route 41 and is well marked. It is mostly an inclined hike, rated moderate to strenuous.
Directions: The entrance to Race Brook Falls is a few miles over the border of Connecticut from Sheffield, MA. From the center of Salisbury take Route 41 north. Pass the border and a few miles later on the left side will be a paved cutoff from Route 41.
Trail Bridge - Robinson State Park - Feeding Hills, MA - Photo Credit Chris Thumm
Robinson State Park

428 North Street Feeding Hills, MA, 01030 Phone: 413-786-2877

20 miles of trails and footpaths are the Yellow, Red, Green, and White Trails, which all connect to each other and will take you through wooded areas and along the scenic Westfield River. Look for the waterfall at Mittineague, too. - Trail Map (PDF)
Hiking Path in Mohawk Trail State Forest - Charlemont, MA - Photo Credit Renee Plasse
Mohawk Trail State Forest

175 Mohawk Trail (MA Route 2) Charlemont, MA, 01339 Phone: 413-339-5504

Hike and walk along the Mohican-Mohawk Trail, a Native American footpath between the Connecticut and Hudson River Valleys. Quarter-mile Thumper Mountain Trail is located near the year-round group campsite, and leads you to a lookout point where you can watch the sun rise. Indian Lookout Trail is one mile long and leads you to another scenic lookout. Hike to Clark Mountain and Todd Mountain from this trail, or continue straight on the Mohican-Mohawk Trail. - Trail Map (PDF)
Hilltop Orchards Hiking - Richmond, MA
Hilltop Orchards Trails

508 Canaan Road - Route 295 Richmond, MA, 01254 Phone: 413-344-6817 Toll-Free: 800-833-6274

Hilltop Orchards, also the home of Furnace Brook Winery, welcomes hikers to explore trails on its 200-acre property in the Berkshire hills. Leashed dogs are allowed on trails. Hikers are asked to sign in at the Farm Winery Store before hiking. Hikers should appropriate shoes and hats, and bring sunscreen and bug repellent. The property has three hikes of easy to moderate difficulty. In winter, the orchard hosts a monthly Full Moon Hike and Bonfire and a Full Moon Snowshoe Trek & Bonfire. Both are guided excursions followed by wine tasting.
Petticoat Hill

Petticoat Hill Road Williamsburg, MA Phone: 413-684-0148

Spend some time in this century old forest

This hillside is covered by a 100-year-old forest criss-crossed by old stone walls and dotted with the cellar holes and foundations of early farmsteads. The Reservation takes its name from the story of a family with seven daughters that settled near the top of the hill. Each daughter wore five petticoats, and, on Monday wash days, people from miles around could see thirty-five petticoats billowing in the breeze as they dried on a clothesline. The focal point of this park is a natural bridge, but visitors can also enjoy swimming, hiking, fishing, and cross-country skiing. Special events are often scheduled.
State Line Trail - Bash Bish Falls State Park - Mount Washington, MA
Bash Bish Falls State Park

Falls Road Mount Washington, MA, 01258 Phone: 413-528-0330

Bash Bish Falls is nestled among 30 miles of trails at Mount Washington State Forest, which includes the South Taconic Trail, and New York's Taconic State Park. Access to the Falls is via a moderately difficult uphill trail. At the top of Mount Everett you can see a vista that includes three states. - Trail Map (PDF)
Norwottuck Rail Trail

Begins at Elwell State Park, Damon Road Northampton, Hadley, & Amherst, MA Phone: 413-586-8706

This 8.5-mile trail runs from Northampton, through Hadley and into Amherst along the old Boston & Main Railroad line. Bicycle and wheelchair hand-cycles rentals are available.
Trail - Chester-Blandford State Forest - Blandford, MA - Photo Credit MA State Parks
Chester-Blandford State Forest

20 Chester Road Chester, MA, 01008 Phone: 413-354-6347

Hike at your own pace on any of this park's many trails. An easy 1-mile hike will lead you to beautiful Sanderson Brook Falls. If you're up to the challenge, the H. Newman Marsh Memorial Trail features a climb to the top of Observation Hill, with views of the river valley. Or, wander near the historic Jacob's Ladder Scenic Byway for another stunning vista. - Trail Map (PDF)
Hiking Trail - Chicopee Memorial State Park - Chicopee, MA
Chicopee Memorial State Park

570 Burnett Road Chicopee, MA, 01020 Phone: 413-594-9416

Wrapped around a 25-acre pond and swimming beache, this park also has walking and biking trails. Hike a two-mile paved trail around the pond and through a pine forest. See trail map for more paths. - Trail Map (PDF)
Forest Trail - Beartown State Forest - Monterey, MA - Photo Credit Steve Laurin
Beartown State Forest

69 Blue Hill Road Monterey, MA, 01245 Phone: 413-528-0904

When you walk or hike through the 12,000 acres of Beartown State Forest, you'll gain endless chances to observe wildlife like beavers, deer, Bob and Fisher cats, and even Black Bears. Hike the 1.5-mile Benedict Pond Loop Trail in any season. Enjoy the stunning, life-filled landscape, and be sure to check out the nearby Appalachian Trail, which runs all the way from Georgia up to Maine. - Trail Map (PDF)
Pedestrian Bridge - CT River Greenway State Park - Northampton, MA - Photo Credit Daniel Griffin
Connecticut River Greenway State Park

136 Damon Road Northampton, MA, 01060 Phone: 413-586-8706

The Connecticut River Greenway connects open spaces and parks. See park website or link below for plenty of walking and hiking opportunities.
Frozen Landscape - Arcadia Nature Center & Wildlife Sanctuary - Easthampton, MA
Arcadia Nature Center and Wildlife Sanctuary

127 Combs Road Easthampton, MA, 01027 Phone: 413-584-3009

Explore four miles of trails at Arcadia, including an 850-foot wheelchair accessible trail. - Trail Map (PDF)
Hours: Open Daily dawn to dusk. Nature Center is open Mon-Fri 9am - 3pm, Saturday 9am - 4pm and Sunday 10am - 2pm.
Laughing Brook Education Center & Sanctuary - Hampden, MA
Laughing Brook Education Center and Sanctuary

793 Main Street Hampden, MA, 01036 Phone: 413-584-3009

This is the house owned by children’s author Thornton Burgess, embedded in 300 acres of walking trails. At least Three designated trails travel through woods and forest, with a variety of plant and animal life to see on all sides. - Trail Map (PDF)
Bear Swamp

Hawley Road Ashfield, MA Phone: 413-684-0148

Visitors to Bear Swamp can explore three miles of trails that lead past an old beaver dam resting atop an old stone milldam, a variety of ferns and woodland wildflowers, and scenic vistas that offer views of nearby apple orchards and the Green Mountains of Vermont beyond. Bear Swamp also features excellent bird watching and picnic tables at the Apple Valley Overlook.
Pittsfield State Forest - Pittsfield, MA - Photo Credit Mark Flapps
Pittsfield State Forest

1041 Cascade Street Pittsfield, MA, 01201 Phone: 413-442-8992

Good for handicap-accessible recreation, fishing, walking & hiking.

Hike or walk 30 miles of trails and enjoy a natural retreat along the ridge of the Taconic Mountain Range, which rises up between Massachusetts and New York. The Taconic Crest Trail is a popular, 35-mile hiking trail. Wheelchair users can easily enjoy the smoother, three-quarter-mile Tranquility Trail. Handicap-accessible picnic site and restroom nearby. - Trail Map (PDF)
Hiking Trail - Sandisfield State Forest (York Lake) - Sandisfield, MA - Photo Credit Kristofer Soberano
Sandisfield State Forest (York Lake)

York Lake Road Sandisfield, MA, 01255 Phone: 413-229-8212

Hike the two-mile Pond Loop Trail for good views of the lake. Moderate difficulty.
Hiking Trail - Mount Grace State Forest - Warwick, MA - Photo Credit Christine Welsh
Mount Grace State Forest

78 Winchester Road Warwick, MA, 01378 Phone: 978-544-3939

Mt. Grace is the second highest peak in Massachusetts. There are hiking, cross-country skiing and horseback riding trails. Picnic areas are also available. - Trail Map (PDF)
Notchview Reservation - Windsor, MA
Notchview Reservation

3 Old Route 9 Windsor, MA Phone: 413-684-0148

This property of forest and field is managed by the Trustees of Reservations has 25 miles of hiking trails, offering easy-to-moderate mountain top hiking. It is open daily, year-round, and is used extensively for cross-country skiing during snow season. It is a popular place to bird watch. Along with the other Trustees hiking properties, events like bonfires and beer tastings are often held in conjunction with a hike. Notchview also offers a dog-friendly trail that winds you through dense forest and over bridge covered rivers.
Hiking Trail - DAR State Forest - Goshen, MA
D.A.R. State Forest

78 Cape Street - MA Route 112 Goshen, MA, 01032 Phone: 413-268-7098

Hike and walk along 15 miles of trails through northern hardwood-conifer forest at the foothill of the Berkshire Mountains. Trails are for multiple uses, including mountain biking, horse riding, and snow sports. Spectacular views of the Connecticut River Valley can be seen from the Goshen fire tower. - Trail Map (PDF)
Trail - Brimfield State Forest - Brimfield, MA - Photo Credit Michael Laferriere
Brimfield State Forest

86 Dearth Hill Road Brimfield, MA, 01010 Phone: 413-267-9687

At Brimfield State Forest, families and groups can walk through mile after mile of green life. Discover something new at every turn along brooks, streams, and the perimeter of Dean Pond, where you can rest at the comfort station. - Trail Map (PDF)
Mount Tom State Reservation - Holyoke, MA - Photo Credit Iris Ortiz
Mount Tom State Reservation

125 Reservation Road Holyoke, MA, 01040 Phone: 413-534-1186

The summit of Mount Tom has vast views of the Connecticut Valley and the Berkshire mountains. The property has 22 miles of hiking and walking trails, visitor center with rest rooms, a play area for kids, picnicking, fishing on the 10-acre Lake Bray; and cross country skiing and ice skating. - Trail Map (PDF)
Monument at Mount Greylock State Reservation - Lanesborough, MA - Photo Credit MOTT
Mount Greylock State Reservation

30 Rockwell Road Lanesborough, MA, 01237 Phone: 413-499-4262

There are many paths of all difficulties which one can take to reach Mount Greylock's summit. For an easier walk, meander along the 1.8-mile-long Bradley Farm Trail, and learn about the area's rich farming history. Also worth exploration are the Scenic Byway or Greylock Glen. Take a camera! - Trail Map (PDF)
mount sugarloaf state resrvation
Mount Sugarloaf State Reservation

Route 116 South Deerfield, MA Phone: 413-545-5993

The summit of Mount Sugarloaf has vast views of the Connecticut River Valley. The park is great for picnics, hiking, and mountain biking. Visitors can use grills, restrooms and picnic areas.
Hours: Summit road is open mid-May through mid-October. Property is open 9 a.m.-sunset
Admission: MA resident , $5; non-MA resident, $10. The pavilion costs $65/day to reserve. It holds 30 people.
Trail Bridge - October Mountain State Forest - Lee, MA
October Mountain State Forest

317 Woodland Road Lee, MA, 01238 Phone: 413-243-1778

This very large state park has extensive walking trails. Be aware you are in black bear country; stay away from bears. - Trail Map (PDF)
Tyringham Cobble

Jerusalem Road Tyringham, MA Phone: 413-298-3239

Visitors to Tyringham Cobble can hike two miles of trails, a section of which is a link in the Appalachian Trail, that pass over the twin knobs of the Cobble offering spectacular views of Tyringham Valley. Small trees and shrubs have taken root among dramatic rock outcrops and glacial boulders, and wildflowers, blackberries, blueberries, and wild strawberries grow in clearings and open meadows. The Cobble was used as pastureland for a Shaker community in the late eighteenth century, but today provides excellent opportunities for bird watching, picnicking, and cross-country skiing.
Bartholomew’s Cobble

Weatogue Road, Ashley Falls Sheffield, MA Phone: 413-229-8600

This National Natural Landmark is home over 800 species of plants, including one of North America's greatest diversities of fern species, as well as abundant wildflowers. The Reservation is named for two rocky knolls that rise above the Housatonic River, and the high point, Hurlburt's Hill, rises 1,000 feet to a twenty-acre field on the Massachusetts-Connecticut border that offers panoramic views northward up the Housatonic River Valley. Visitors will enjoy hiking this diverse woodland, and the many public programs that are presented throughout the year.
Chapelbrook - Ashfield, MA - Photo Credit Trustees of Reservations

Williamsburg Road Ashfield, MA, 01330 Phone: 413-684-0148

At the core of Chapelbrook is Pony Mountain, whose nearly vertical 100-foot rock face offers a challenge to very skilled, technical rock climbers. A gentle, half-mile trail leads around the western side of Pony Mountain to its summit, offering unobstructed views south toward the Berkshire foothills. Chapelbrook is also popular for its sometimes-torrential Chapel Falls. The steady trickle of Chapel Brook becomes a deluge in spring, but in summer, the pools that form under the falls offer a cool, welcome dip.
Monroe State Forest

Tilda Hill Road Monroe, MA Phone: 413-339-5504

Walking and hiking in Monroe State Forest will lead you through valley, mountain, and woods. For scenic views of Hoosac and Green Mountains and Deerfield River, hike to the summit of Spruce Mountain. Try the Dunbar Brook Trail, which starts from the River Road parking area and is full of ancient trees. The brook drops 700 feet and gives way to waterfalls, rapids, and natural pools. No services are available. Watch for black bears. Trail map.
Dry Hill

Old North Road (Harmon Road) New Marlborough, MA, 01230 Phone: 413-298-3239

About 200 acres of forest can be traversed on a mile-long loop trail that traces a small brook and passes vernal pools and other wetlands. The trail passes a stream, several spring ponds, and a red maple and hemlock swamp. An oak forest covers the upper slopes and ridge tops. Dense thickets of mountain laurel bloom in late June. Trails are moderately difficult.
Open year-round, daily, sunrise to sunset. Allow a minimum of one hour for the walk.
Information: www.thetrustees.org/places-to-visit/berkshires/dry-hill.html
Skinner State Park

Route 41 Hadley, MA Phone: 413-586-0350

This park features 10 miles of trails, which allow visitors to climb Mount Holyoke and the Holyoke Range. Offers great view of the Connecticut River Valley.
Field Farm

Sloan Road Williamstown, MA Phone: 413-458-3144

Field Farm’s over four miles of trails offer excellent hiking, cross-country skiing, and snowshoeing opportunities in the shadow of Mount Greylock, Massachusetts’ highest peak. A center of agriculture since at least 1750, Field Farm also features a modernist house now utilized as a bed and breakfast (The Guest House at Field Farm), and the 1965 Ulrich Franzen designed “Folly” – a pinwheel shaped guest house open for tours during the summer.
Glendale Falls

Clark Wright Road Middlefield, MA Phone: 413-684-0148

Fed by more than five square miles of watershed, Glendale Falls is one of the longest and most powerful waterfall runs in Massachusetts. In spring, the waters of Glendale Brook roar over rock ledges more than 150 feet high before joining the Westfield River. A quarter-mile trail leads to bottom of the falls for viewing. The Reservation was once part of the historic 18th-century Glendale Farm, which operated a gristmill whose foundation can be explored in the woods just north of the falls.

New Marlborough Hill Road New Marlborough, MA Phone: 413-298-3239

A seventeen-acre upland field of native meadow wildflowers attracts a variety of dragonflies and butterflies

Questing features two miles of trails perfect for hiking or cross-country skiing, extensive tracts of hardwood forest, and a seventeen-acre field of native meadow wildflowers that attracts a variety of dragonflies and butterflies. Cellar holes and stone walls, tell the story of the 200-year-old settlement known as Leffingwell, where the first non-Native American children were born in Berkshire County. This settlement was abandoned in the late nineteenth century as farmers migrated to the Midwest.
Hiking View - Mount Washington State Forest - Mt. Washington, MA - Photo Credit MA State Parks
Mount Washington State Forest

545 East Street Mount Washington, MA, 01258 Phone: 413-528-0330

Take in vast views of this rugged natural landscape along two main trails. The South Taconic Trail brings you to the 2,000-foot summit of Alander Mountain. Or, you can follow the majestic Appalachian Trail; either way, explore this area on foot for a satisfying view of the surrounding valley ridges and trees. - Trail Map (PDF)
Taconic Crest Trail - Williamstown to Pittsfield, MA
Taconic Crest Trail

This is a 35-mile north/south trail with great vistas. The trail meanders in or near western Massachusetts, from Williamstown to Pittsfield. The trail heads up into Vermont and moves back and forth along the New York and Massachusetts state borders. Petersburg Pass adjacent to Williamstown is the most popular starting point. A wheelchair-accessible picnic area and restroom are located nearby.
How to Find It: From Route 7 in Williamstown, MA, turn onto Route 2 west at the A-Frame Bakery. At the top of the hill is a large parking area on the left. Park there, and cross the road to get onto the trail head to the Snowhole near Vermont state line or just head south to Berlin Mountain by hiking up the trail leading up the hill at the back of the parking lot.