Top Things to Do in Williamstown & the Berkshires

Our property offers four miles of easy to moderate hiking trails (trail map PDF) for self-guided exploration. For guided hiking tours of the property, please contact us for more information and to schedule. In addition to our trails, you’ll find a variety of nearby hiking options that showcase the stunning natural beauty of the Berkshires.

On Property Hiking Trails

• North Trail
  Beyond the lawn surrounding the Guest House, follow the popular mile-long North Trail, which circles the centrally located pasture in a wide loop and affords mountain views in all directions.
• Oak Loop Trail
  A half-mile extension from the North Trail, crossing a flowing stream and passing through a mature oak forest filled with abundant ferns.
• Caves Trail Loop
  Another half-mile loop leading through small streams that disappear into underground channels and caves carved over the millennia.
• Pond Trail
  A 0.4-mile trail starting from the trailhead parking lot, winding around the pond—a great short, scenic walk.
• South Trail
  A 1.7-mile trail beginning across the street from the Pond Trail, with open fields and woodlands, dappled with sunshine filtering through the trees.

Nearby Hiking Trails

• Mountain Meadow Preserve (Williamstown, MA—Trustees Property)
  4 miles of trails through varied habitats, perfect for birdwatching and views of Mount Greylock.
• Notchview (Windsor, MA—Trustees Property)
  Extensive trail network across 3,000 acres for hiking, birdwatching, and cross-country skiing.
• Ashley House (Sheffield, MA—Trustees Property)
  Easy trails with educational signage highlighting its historical significance related to Mum Bett.
• Bartholomew’s Cobble (Sheffield, MA—Trustees Property)
  5 miles of trails with diverse habitats, including fields and marshes along the Housatonic River.
• Monument Mountain (Great Barrington, MA—Trustees Property)
  3-mile loop to Peeskawso Peak with views that inspired Herman Melville and Nathaniel Hawthorne​.
• Ashuwillticook Rail Trail (Cheshire, MA)
  Flat and easy path, making it suitable for walking and biking, with beautiful river views.
• Mount Greylock State Reservation (Lanesborough, MA)
  Multiple hiking trails at Massachusetts’ highest point, with diverse landscapes and ecosystems.
• Natural Bridge State Park (North Adams, MA)
  Short, easy trails leading to unique geological features like a marble arch.

Waterfall Hikes

• Money Brook Falls (Williamstown, MA)
  Short, steep trail in Mount Greylock State Reservation with marvelous 80’ waterfall.
• Cascade Trail  (North Adams, MA)
  1.5-mile scenic hike with beautiful waterfalls and lush forest, suitable for hikers of various skill levels.
• Doane’s Falls (Royalston, MA—Trustees Property)
  A series of plunging falls along Lawrence Brook with a short, scenic trail surrounded by lush greenery.
• Glendale Falls (Middlefield, MA—Trustees Property)
  A quarter-mile trail leads to the bottom of one of the longest and most powerful waterfall runs in MA.
• Wahconah Falls State Park (Dalton, MA)
  Short but picturesque hike with views of the falls and surrounding forest.
• Bash Bish Falls State Park (Mount Washington, MA)
  Known as the tallest waterfall in Massachusetts, beautiful views with 1-mile round trip hike.

After exploring the on-property Bloedel Collection, venture out to discover many wonderful places to enjoy culture in Williamstown and the surrounding area. Several world-class art museums are open throughout the year.

On Property: The Bloedel Collection

• Guest House Interior Art & Design
  View a curated collection of mid-century modern furniture, modern paintings, and design elements.
• Sculpture Garden
  Take a self-guided tour to explore 13 permanent sculptures in the surrounding gardens.
• ‘The Folly’ Museum at Field Farm
  An architectural masterpiece by Ulrich Franzen. Exclusive tours are available for guests of the Inn upon request.

Nearby Options

• The Clark Art Institute (Williamstown, MA)
  Art museum and research center known for its extensive collection of European and American art, with a focus on French Impressionism.
• Williamstown Art Conservation Center (Williamstown, MA)
  The largest regional conservation center in the country, located at The Clark Art Institute.
• Williams College Museum of Art (Williamstown, MA)
  A college-affiliated museum with 15,000 works spanning contemporary and modern art.
• Ashley House (Sheffield, MA—Trustees Property)
  Known for its connection to Mum Bett (Elizabeth Freeman), a woman who helped end slavery in Massachusetts after winning her freedom.
• Naumkeag (Stockbridge, MA—Trustees Property)
  Famous for 8 acres of terraced gardens and landscaped grounds surrounded by 40 acres of woodland, meadow, and pasture.
• Mission House (Stockbridge, MA—Trustees Property)
  Colonial-era house and museum and garden tells the story of the Stockbridge Mohicans and missionary John Sergeant.
• Berkshire Botanical Garden (Stockbridge, MA)
  A 15-acre public garden offering diverse horticultural displays and educational programs.
• The Norman Rockwell Museum (Stockbridge, MA)
  Honoring Stockbridge’s native son, with the largest collection of his work and American illustration art.
• Hancock Shaker Village (Pittsfield, MA)
  A living history museum showcasing Shaker life through restored buildings, artifacts, and farm demonstrations.
• MASS MoCA (North Adams, MA)
  One of the largest contemporary art centers in the U.S., with visual, performing, and media arts within a unique factory campus.
• Bennington Museum (Bennington, VT)
  Features New England art and history, including the largest public collection of works by Grandma Moses.
• Art Lovers Weekend Itinerary
  Enjoy a carefully curated itinerary for a weekend filled with art in the Berkshires.

• Kripalu (Stockbridge, MA)
  Renowned yoga and wellness center offering classes, workshops, and day programs.
• Tasha Yoga (Williamstown, MA)
  A yoga studio offering a variety of yoga classes in a supportive environment.
• InTouch Massage & Day Spa (Williamstown, MA)
  Offers a range of massage therapies, facials, and body treatments in a relaxing environment.
• Seven Salon Spa (Stockbridge, MA)
  Provides a variety of spa services including massages, facials, and beauty treatments.

• Mezze Bistro & Bar
  A Mediterranean-inspired restaurant offering farm-to-table dishes and craft cocktails.
• Bluebird & Co
  Serves globally inspired, locally sourced ingredients, creative craft cocktails, and an inviting atmosphere.
• State Food + Drink
  West Coast-inspired, local cuisine with seasonal and sustainable ingredients, centered on community.
• The Barn Kitchen & Bar
  Focuses on American cuisine with locally sourced ingredients, great for brunch and dinner.
• Blue Mango
  Thai and Japanese fusion restaurant known for its innovative approach to traditional cuisine.
• Spice Root
  An Indian restaurant offering a variety of authentic dishes in a comfortable setting.

The Berkshires is an arts mecca where visitors can enjoy so much live stage! When planning your visit be sure to check out the following:

• ‘62 Center for Theatre, Music, and Dance (Williamstown, MA)
  A multi-venue performing arts center at Williams College.
• Berkshire Theatre Group (Stockbridge & Pittsfield, MA)
  Leading arts organization with multiple stages on two campuses.
• Barrington Stage (Pittsfield, MA)
  Known for its innovative productions and focus on new plays and musicals.
• Shakespeare and Company (Lenox, MA)
  Specializes in classical theatre, primarily Shakespeare.
• Jacobs Pillow (Becket, MA)
  A renowned dance festival and educational center.

• Destination Williamstown
  An online guide offering a comprehensive calendar of events, festivals, and attractions in the area.
• Winterlights at Naumkeag (Stockbridge, MA)
  An annual event at Naumkeag transforming the gardens into a festive display of holiday lights.
• Daffodil and Tulip Festival (Stockbridge, MA)
  A springtime festival at Naumkeag showcasing thousands of blooming daffodils and tulips.
• Berkshire International Film Festival
  An annual event showcasing independent films from around the world.
• Williamstown Theatre Festival (Williamstown, MA)
  An annual summer festival featuring world-class theatre productions and performances.
• The Clark Art Institute (Williamstown, MA)
  Offers rotating exhibitions, performances, and workshops for all seasons.
• MASS MoCA Events (North Adams, MA)
  One of the largest contemporary art centers in the U.S., offering events year-round.
• Solid Sound Festival (North Adams, MA)
  A biannual music and arts festival curated by the band Wilco, held at MASS MoCA.
• FreshGrass Festival (North Adams, MA)
  An annual bluegrass and roots music festival hosted at MASS MoCA.
• Jacob’s Pillow Dance Festival (Becket, MA)
  A renowned summer dance festival featuring performances from international dance companies.
• Tanglewood Music Festival (Lenox, MA)
  The summer home of the Boston Symphony Orchestra, showcasing diverse musical performances.

• Destination Williamstown
  An online guide offering a comprehensive directory of boutiques and businesses in the area.
• Purple Plume (Williamstown, MA)
  A women’s clothing and accessories boutique offering a curated selection of apparel and gifts.
• Where’d You Get That?! (Williamstown, MA)
  An eclectic shop featuring a wide range of toys, games, puzzles, and quirky gifts for all ages.
• Goff’s Sports (Williamstown, MA)
  A local store providing sports equipment, apparel, and footwear, including outdoor and athletic gear.
• The Clark Museum Store (Williamstown, MA)
  Features art books, prints, jewelry, and unique gifts inspired by the museum’s collections.
• Bennington Potters (Bennington, VT)
  Known for handcrafted stoneware pottery, offering functional and decorative pieces made on-site.

• Bright Ideas Brewing (North Adams, MA)
  Located at MASS MoCA, it offers a variety of craft beers in a vibrant atmosphere.
• Shire Breu-Hous (Dalton, MA)
  Brewery and restaurant, providing house-made beers alongside a full dining menu.
• Big Elm Brewing (Sheffield, MA)
  Known for its locally brewed ales and lagers, it provides weekend tastings and sells beers to-go.
• Berkshire Cider Project (North Adams, MA)
  Crafts modern, dry ciders from regional apples, emphasizing sustainability and local agriculture.
• Hilltop Orchards (Richmond, MA)
  Home of Furnace Brook Winery, offering hard cider and wine like the award-winning Johnny Mash cider.
• Balderdash Cellars (Richmond, MA)
  A boutique winery producing small-batch wines with grapes sourced from top vineyards.
• Les Trois Emme Winery (New Marlborough, MA)
  family-owned winery offering traditional wines and unique options like Stingy Jack’s Pumpkin Wine.
• Berkshire Mountain Distillers (Sheffield, MA)
  Renowned for its small-batch spirits, including the acclaimed Ethereal Gin, and offers tours and tastings.

• Ramblewild (Lanesborough, MA)
  Treetop adventure park featuring high wires, ziplines, and obstacle courses for an exhilarating day in the forest canopy.
• Jiminy Peak (Hancock, MA)
  Adventure park offering a variety of activities including multi-zipline course, mountain coaster, alpine super slide, and scenic chairlift rides.
• Zoar Outdoor (Charlemont, MA)
  Offering thrilling whitewater rafting, zip line canopy tours, and kayaking along the Deerfield River for adventure seekers of all ages.
• Berkshire Outfitters (Adams, MA)
  Rent canoes, kayaks, and stand-up paddleboards for exploring nearby lakes and rivers, with options for one and two-person rentals.
• SUP, Canoe & Kayak
  Here’s a comprehensive guide for individuals interested in canoeing, kayaking, or rafting on the Hoosic River.
• Berkshire Rivers Fly Fishing
  Offering guided fly fishing trips, lessons, and equipment rentals. All excursions are suitable for beginners and experts alike.

• Destination Williamstown
  An online guide offering a comprehensive calendar of events, including farmers markets, festivals, and attractions in the area.
• Williamstown Farmers Market
  Offers local produce, baked goods, crafts, and live music every Saturday from May to October.
• North Adams Farmers Market
  A community market featuring fresh produce, artisanal foods, and handmade crafts on Saturdays from June to October.
• Bennington Farmers Market
  A year-round market providing local produce, meats, dairy, baked goods, and crafts, held on Saturdays.
• Berkshire Grown
  Keep Farmers Farming! Here you can find local farmers’ markets, events, food in Restaurants, and workshops to support our community.

• Art Lovers Weekend in the Berkshires
  A weekend itinerary that highlights iconic art destinations, including visits to Naumkeag for its historic gardens, MASS MoCA for contemporary art, and The Clark Art Institute.
  
• Weekend in the Berkshires
  This two-day itinerary explores iconic destinations like Naumkeag, Bartholomew’s Cobble, and Mountain Meadow Preserve. Highlights include the Blue Steps and gardens at Naumkeag, diverse flora at Bartholomew’s Cobble, and the scenic views of the Williamstown area.
  
• NYC to Berkshires
  Designed for visitors traveling from New York City to the Berkshires, covering 14 recommended places, such as Naumkeag, Monument Mountain, and Bartholomew’s Cobble. The itinerary combines art, history, and nature for a well-rounded weekend escape.
• Winter Weekend
  Suggested activities include snowy walks, skiing at Notchview, and visits to art destinations like The Clark Museum and MASS MoCA. Guests can also enjoy a dazzling holiday display at Winterlights at Naumkeag.

• Snowshoeing
  Enjoy snowshoeing on property with 4 miles of trails (trail map PDF) and complimentary snowshoes available for B&B guests. Please note that poles are not provided.
• Cross-Country Skiing
  Bring your gear to hit the trails right outside the Guest House, or travel 30 minutes to our sister property Notchview or nearby Prospect Mountain for groomed trails and rentals.
• Mount Greylock (Lanesborough, MA)
  Explore winter hiking trails at Mount Greylock, the highest point in Massachusetts.
• Jiminy Peak (Hancock, MA)
  Enjoy winter skiing and snowboarding at one of the largest ski resorts in southern New England.
• Winter Weekend in the Berkshires Itinerary
  Explore a carefully curated itinerary for a winter weekend filled with activities.