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10 Lesser-Known Towns In The Berkshires You Must Visit

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by Marcella Stouffer

10-lesser-known-towns-in-the-berkshires-you-must-visit

Are you tired of visiting the same old tourist spots? Ready for something new? The Berkshires, known for its stunning landscapes and cultural attractions, has hidden gems waiting for you. These lesser-known towns in the Berkshires offer unique experiences, from charming main streets to outdoor adventures. Imagine strolling through quaint villages, discovering local art, and enjoying farm-to-table dining without the crowds. Whether you're into hiking, history, or just relaxing, these towns have something special. Get ready to explore places that will make your trip unforgettable. Let's dive into the heart of the Berkshires and uncover its best-kept secrets.

Hidden Gems in The Berkshires

The Berkshires, a picturesque region in western Massachusetts, is known for its rolling hills, cultural attractions, and charming small towns. While many visitors flock to popular spots like Lenox and Stockbridge, there are several lesser-known towns that offer unique experiences and hidden treasures. Here are ten towns in The Berkshires you must visit.

1. Sheffield

Sheffield, one of the oldest towns in The Berkshires, boasts a rich history and stunning natural beauty.

  • Bartholomew's Cobble: A National Natural Landmark with unique rock formations and diverse plant life.
  • Sheffield Historical Society: Learn about the town's history through exhibits and events.
  • Covered Bridge: Visit the historic covered bridge for a picturesque photo opportunity.

2. New Marlborough

New Marlborough offers a peaceful retreat with its scenic landscapes and charming village center.

  • Umpachene Falls Park: A serene spot for picnicking and enjoying the cascading waterfalls.
  • Gedney Farm: Stay at this historic farm-turned-inn and savor farm-to-table dining.
  • The Old Inn on the Green: Dine at this historic inn known for its gourmet cuisine.

3. Monterey

Monterey, a small town with a big heart, is perfect for outdoor enthusiasts and art lovers alike.

  • Lake Garfield: Enjoy swimming, boating, and fishing at this beautiful lake.
  • Bidwell House Museum: Explore this 18th-century homestead and its surrounding gardens.
  • Monterey General Store: Stop by this historic store for local goods and a taste of small-town life.

4. Tyringham

Tyringham, a hidden gem, offers tranquility and stunning vistas.

  • Ashintully Gardens: Wander through these enchanting gardens and admire the ruins of the Ashintully mansion.
  • Tyringham Cobble: Hike to the top for panoramic views of the valley.
  • Santarella Gingerbread House: Visit this whimsical house and its unique architecture.

5. West Stockbridge

West Stockbridge, a vibrant town with a thriving arts scene, is a must-visit for culture enthusiasts.

  • TurnPark Art Space: Explore this outdoor sculpture park and cultural center.
  • Shaker Mill Books: Browse through a vast collection of rare and used books.
  • Six Depot Roastery & Café: Enjoy locally roasted coffee and delicious pastries.

6. Richmond

Richmond, a quaint town with a strong agricultural heritage, offers a taste of rural life.

  • Hilltop Orchards: Pick your own apples and sample cider at this family-owned orchard.
  • Richmond Pond: Relax by the water or take a kayak out for a paddle.
  • Balderdash Cellars: Visit this boutique winery for a tasting of their handcrafted wines.

7. Cheshire

Cheshire, nestled in the northern Berkshires, is known for its outdoor recreation opportunities.

  • Ashuwillticook Rail Trail: Bike or walk along this scenic trail that runs through the town.
  • Cheshire Reservoir: Fish, boat, or simply enjoy the views at this large reservoir.
  • Cheshire Cheese Shop: Sample local cheeses and other gourmet treats.

8. Savoy

Savoy, a small town with big natural attractions, is perfect for nature lovers.

  • Savoy Mountain State Forest: Hike, camp, or picnic in this expansive state forest.
  • Tannery Falls: Discover this hidden waterfall tucked away in the forest.
  • Savoy Hollow General Store: Grab a bite to eat and chat with the friendly locals.

9. Lanesborough

Lanesborough, a town with a rich history and beautiful landscapes, offers a variety of activities.

  • Mount Greylock: Hike to the highest peak in Massachusetts for breathtaking views.
  • Pontoosuc Lake: Enjoy boating, fishing, or a relaxing day by the water.
  • The Old Stone Store: Visit this historic building, now a museum and gift shop.

10. Hinsdale

Hinsdale, a quiet town with a strong community spirit, is a great place to unwind.

  • Ashmere Lake: Swim, fish, or paddle in this peaceful lake.
  • Hinsdale Dayz: Join the locals for this annual summer festival with food, music, and fun activities.
  • Bascom Lodge: Stay at this rustic lodge on Mount Greylock and enjoy the stunning views.

Hidden Gems Await

The Berkshires offer more than just popular tourist spots. Lesser-known towns like Sheffield, Monterey, and New Marlborough provide unique experiences. Sheffield boasts antique shops and scenic views. Monterey offers Lake Garfield for water activities. New Marlborough has charming inns and local eateries.

West Stockbridge and Richmond are perfect for art lovers and history buffs. West Stockbridge features galleries and a vibrant art scene. Richmond has historical sites and beautiful landscapes.

Hinsdale, Savoy, and Florida are ideal for nature enthusiasts. Hinsdale's trails, Savoy's state forest, and Florida's mountain views offer outdoor adventures.

Egremont and Mount Washington round out the list with their quaint charm and natural beauty. Egremont's local shops and Mount Washington's hiking trails are must-visits.

Exploring these towns reveals the true essence of the Berkshires. Plan your trip and uncover these hidden gems.