Dream Time In The Berkshires



Briarcliff Motel, 506 Stockbridge Road, Great Barrington. 413-528-3000. As cheerful as its British owners, this transformation of a 60’s motor lodge into a colorful and cozy 16-room (two are pet friendly) bed and breakfast is a jolly good choice for families (including skiers in the winter) pitching up in the southern Berkshires. www.thebriarcliffmotel.com

Cranwell Resort, Spa and Golf Club, 55 Lee Road, Lenox. 413-637-1364. Offering 114 guest rooms, suites, cottages and townhouses, this historic hilltop Tudor-style mansion calls itself “the ultimate resort experience on 380-acres snuggled in the heart of the Berkshires.” Consider “snuggled” your warm and fuzzy invite. www.cranwell.com

The Barrington, 281 Main St., Level 3, Great Barrington. Tel: 413-528-6159. Occupying the top floor of an 1880’s warehouse in the heart of Great Barrington’s historic downtown, this eclectic charmer, accepting kids 10 and older, features six spacious, newly updated salon-suite rooms. www.thebarringtongb.com

The Guest House at Field Farm, 554 Sloan Road, Williamstown. 413-458-3135. Step back in time at this 1948 Bauhaus-inspired home, now a transporting six-room bed & breakfast filled with midcentury modern furnishings, books and art. Set on 316 acres with landscaped gardens, hiking trails, peerless Mount Greylock views, outdoor sculptures and more, this kid-free sanctuary is perfect for adult alone time. www.thetrustees.org/field-farm


Allium Restaurant + Bar, 42/44 Railroad Street, Great Barrington. Tel: 413-528-2118. Devoted to supporting local farms and artisan producers, this rave-reviewed farm-to-table hotspot (along with sister property Mezze Bistro + Bar in Williamstown) is a standout in foodie haven Great Barrington. www.alliumberkshires.com

Baba Louie’s, 34 Depot Street, Pittsfield. Tel: 413-499-2400. Also in Great Barrington (286 Main Street, Tel: 413-528-8100), this popular family-friendly pizza joint serves wood-fired pies with fresh ingredients and flavors for all tastes. www.babalouiespizza.com

Dream Away Lodge, 1342 County Road, Becket. Tel: 413-623-8725. Feed your belly with Chef Amy Loveless’ hearty comfort food and then hang with the locals and hear live music as owner Dan Osman keeps the magic alive at this legendary mountaintop haunt where Bob Dylan and friends once rolled through. www.thedreamawaylodge.com

Monterey General Store, 448 Main Road, Monterey. Tel: 413-528-5900. Proprietor Scott Cole, a former restaurateur, preserves mercantile tradition from 300 years ago at this rustic riverside eatery and store housed in a 1780 post and beam structure. www.monterey-general-store.com

Pappa Charlie’s Deli, 28 Spring Street, Williamstown. Tel: 413-458-5969. Since 1976, this Williams College institution has served sandwiches named after the stars of the annual Williamstown Theater Festival. Gwyneth Paltrow? Richard Chamberlain? Neil Patrick Harris? Here, it’s not watch what you eat, but who.


Bartholomew’s Cobble, 105 Weatogue Road, Ashley Falls, Sheffield. Tel: 413-229-8600. Originally an inland sea from some 500 million years ago, this geological wonder was literally flipped upside down by the tectonic formation of the Taconic and Berkshire Mountains. Hike up 1,000-foot Hurlburt’s Hill for an overview, then visit the Ashley House to see where slavery in Massachusetts ended. www.thetrustees.org/places-to-visit/berkshires/bartholomews-cobble.html

Mount Greylock, Visitor Center, 30 Rockwell Road, Lanesborough. Tel: 413-499-4262. Massachusetts’ first wilderness state park (1898) and highest mountain (3,491 feet) is a true peak performer, featuring jaw-dropping panoramic views; seasonal overnights and dining at the 1930’s Bascom Lodge (413-743-1591); and hiking galore. Presently under repair, the 93-foot War Memorial tentatively reopens in 2016. mount.greylock@state.ma.us

Monument Mountain, Route 7, Great Barrington. Tel: 413-298-3239. Rising above the Housatonic River Valley, this storied peak is rich with history, from Native American trails to carriageways once traveled by Ford Model T’s. The three loop trails are short but steep, so bring water, sturdy shoes—and your camera.


Arrowhead, 780 Holmes Road, Pittsfield. Tel: 413-442-1793. Part of the six-member Berkshire 18th Century Trail (www.berkshire18thcenturytrail.org), this farmhouse is where Herman Melville, inspired by Mount Greylock’s distant humps, penned Moby-Dick. Required reading—and visit—for all ages. www.mobydick.org

Cricket Creek Farm, 1255 Oblong Road, Williamstown. Tel: 413-458-5888. Renowned for its artisanal cheese, this grass-based dairy farm welcomes visitors for tours, events and monthly cheese-making classes. Bring your picnic basket and fill up with honey, jams, cider, mustard and other goodies from local producers at the farm store. www.cricketcreekfarm.com

Hancock Shaker Village, 1843 West Housatonic Street, Pittsfield. Tel: 413-443-0188. The nation’s most authentic and complete Shaker community, this National Historic Landmark offers free admission to children 12 and under traveling with their families. Don’t miss the baby animals each April into early May. www.hancockshakervillage.org

Historic Deerfield, 80 Old Main Street, Deerfield. Tel: 413-774-5581. Surrounded by working farms and rolling fields, this uniquely authentic 331-year-old village is time travel defined. www.historic-deerfield.org

Kidspace at Mass MoCA, 1040 Mass MoCA Way, North Adams. Tel: 413-662-2111. No “kidified” space, this bright gallery/studio concept engages children—and parents—in serious thought and dialog about art, social issues, the self, and more. www.massmoca.org

Ramblewild, 110 Brodie Mountain Road, Lanesborough. Tel: 844-472-6253. Constructed without putting nails or screws in a single tree, North America’s largest tree-to-tree aerial adventure park uniquely combines an innovative approach to sustainable forestry with exhilarating ropes courses. www.ramblewild.com

Zoar Outdoor, 7 Main Street, Route 2, Charlemont. Tel: 413-339-4010. Since 1989, this outdoor adventure operator has provided instruction, guidance and rentals for whitewater rafting, canoeing, kayaking and rock climbing. With 30-plus miles of hiking and mountain biking trails, plus camping and lodging options, there something for all ages. www.zoaroutdoor.com

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