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Berkshires and Pioneer Valley have lovely & mountainous places to walk

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

Many trails to choose from

Jiminy Peak offers the most extensive lift-served mountain biking in the Berkshires, not to mention loads of gorgeous hiking trails. Additionally, Jiminy Peak Mountain Resort is the largest ski and snowboard resort in southern New England, summer home to Mountain Adventure Park and the only mountain resort in North America to generate its own energy using alternative wind power. Since opening in 1948 Jiminy Peak has evolved to become a 4 season resort, offering something for everyone. Our mission is to provide positive, memorable, Mountain Resort experiences with outstanding, friendly and helpful service in remarkably beautiful surroundings; inspiring guests to return again and again.

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.

143 East Street South Egremont, MA, MA Phone: 413-528-0330

Good for scenic views, wilderness camping, fishing, hiking, and picnicking. Free access.

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. See Mount Washington State Forest for full description of park.

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.

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 as well as butterflies, wetland amphibians, and numerous small mammals and reptiles. One trail encircles and cuts through a spectacular upland wildflower meadow. A second loop trail enters the woodland, where it leads up a hill to a summit with views of Mount Greylock and the Taconic Range.

1041 Cascade Street Pittsfield, MA 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. Click here to read a full description of Pittsfield State Forest.

472 West Mountain Road Lenox, MA 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. Open year-round. Trails are open dawn to cusk. Email: berkshires@massaudubon.org

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

With two peaks, this site offers great views of the surrounding countryside. It features hiking trails and scenic picnic spots. South peak accessible by automobile.

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

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

Good for paddling, picnics, swimming, fishing, and views

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. See Robinson State Park for full description of this 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.

Taconic Crest Trail

This is a 35 mile north/south trail with great vistas, hardwood forests, and side trails. 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 destination along the trail. The trail shows classic New England geology and scenery. The paved three-quarter mile Tranquility Trail is popular with wheelchair-users and other visitors who favor its smooth surface. 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 Taconic Park Restaurant approximately half way between the Store at Five Corners and the Williams Inn. (This road is known locally as the Taconic Trail.) At the top of the hill is a large parking area on the left. Park there, and cross the road to access 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.

Mount Everett Road Mount Washington, MA Phone: 413-528-0330

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

This 1,356-acre state reservation is a great choice for fans of scenic summit views who want a shorter hike. In season, walk a 0.75-mile path to reach the top of 2,624-foot Mount Everett. Seasonal road access and to parking at the Guilder Pond day-use area. At the 2,624-foot summit is a breathtaking panorama of Massachusetts, New York, and Connecticut. Enjoy a picnic at Guilder Pond which features a spectacular display of blooming mountain laurel and azalea in the spring. The Appalachian Trail winds its way along the ridgeline and through Sage's Ravine.
Parking in designated areas only. No services are available. Carry-in, carry-out all belongings and trash. Take precautions to avoid ticks; be aware of bears and rattlesnakes. Pets must be on a 10-foot maximum leash. Motorized off-road vehicles and alcoholic beverages are prohibited.
Season & Hours: The park is open year-round, sunrise to sunset year-round.

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 full description of Chesterfield Gorge.

Route 20 Chester, MA Phone: 413-354-6347

Good for walking & hiking, horseback riding, hunting (restrictions), mountain biking, fishing

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.
See Chester-Blandford State Forest for full description of this park.

793 Main Street Hampden, MA Phone: 413-566-8034

An 18th century house owned by children’s author Thornton Burgess highlights the 354 acres of walking trails and natural beauty. A library and exhibits offered.

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

Good for non-motorized boating, walking & hiking, camping, snowmobiling; fishing; leashed pets allowed

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.
See Beartown State Forest for full description of this park.

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.

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

Good for camping, hiking, boating; non-motor boats only

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. See Clarksburg State Park for full description of this park.

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

The nature center features 25 acres of varied terrain, with five miles of trails and an observation tower. The 700-acre sanctuary includes a floodplain forest, marshes, and a grassland habitat.

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

Hiking trails available in this state forest, open Memorial to Labor Days

Hike the two-mile Pond Loop Trail for good views of the lake. Moderate difficulty. Or use this Trail Map.
See full description of Sandisfield State Forest.

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.

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.

Williamsburg Road Ashfield, MA 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.

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

Good for hiking & walking, picnicking, horseback riding; fishing

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.
See Brimfield State Forest for full description of this park.

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.

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

Good for year-round camping, viewing nature & wildlife, and trout fishing.

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 and set over the landscape. Indian Lookout Trail, located on the other side of the forest, is one-and-a-quarter miles 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. See Mohawk Trail State Forest for full description of park.

136 Damon Road at Route 9 Northampton, MA 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.

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

Handicap-accessible hiking and camping; water sports, picnicking, hiking, camping, paddling, pets allowed

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. See Savoy Mountain State Forest for full description of park.

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.

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

Swimming and fishing on a large pond; walking trails

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. The park is open daily, 8 a.m-4 pm. Trail map.

Woodland Road Lee, MA 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 See full description of October Mountain State Park

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

Good for boating, hiking, fishing, horseback riding, and winter sports; pets permitted except on sandy beach; non-motorized boats only.

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; Recommended hikes See DAR State Forest for full description of this park.

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.

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 busines. 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.

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

Good for hiking and picnicking; fishing; leashed pets allowed

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.
See Bash Bish Fall State Park for full description of this park.

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.

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.
Carry-in and carry-out all trash. Black bears live here. Never confront or feed or tease the bears. Seal you rfood. Rattlesnakes live in the park. Stay clear of them. Pets are permitted on a 10-foot leash. Off-road vehicles and alcoholic beverages are not allowed.
Trail map.

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

Good for hiking, camping, scenic drives, and viewing wildlife.

There are many paths of all difficulties which one can take to reach Mount Greylock's summit. Find suggested hiking paths at http://1.usa.gov/1m4suRn. 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! See Mount Greylock State Reservation for full description of this park.

78 Warwick 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.

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.

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.

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.

99 Millers Falls Road Northfield, MA Phone: 800-859-2960

This year-round recreation property has 26 miles of trails for hiking and mountain biking. See full description of Northfield Mountain Recreational and Environmental Center

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.

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

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

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.

508 Canaan Road / Route 295 Richmond, MA Phone: 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. A fee of $5 per person is used for land preservation. Hikers should appropriate shoes and hats, and bring sunscreen and bug repellent.
The property has three hikes. The easy hike goes to the top of the orchard, where visitors may sit at the picnic table and enjoy the 20-mile views. For the easy-to-moderate hike, take the Johnny Mash II wooded country trail, which is one mile long. The terrain is flat and follows the Furnace Brook creek to a forest of majestic hemlocks. This hike takes about one hour round-trip. For a moderate hike, followed the Johnny Mash 1 trail when it connects to the new Perry's Peak trail. This leads to a 2.2-mile loop beginning at the Farm Winery Store and heading up through the orchard with twists and turns in and out of the woods.
In winter, the orchard hosts a monthly Full Moon Hike & Bonfire and a Full Moon Snowshoe Trek & Bonfire. Both are guided excursions followed by wine tasting.

Peck Road Wales, MA Phone: 413-267-9654

There are guided spring wildflower walks at this 3,000-acre site, which features three miles of nature trails and two museums.

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.

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.