Things to Do in the Berkshires, Massachusetts

The Berkshires invite you to slow down, explore deeply, and find your own rhythm. Known for its mountain views, storied cultural institutions, and vibrant towns, this corner of Massachusetts blends natural beauty with artistic soul. Whether you’re here for a weekend escape or a longer retreat, there’s plenty to discover beyond our lakefront grounds.

Find your bearings with our interactive map, a curated guide to the region’s trails, hidden lakeside spots, and local favorites. Whether planning a scenic drive, a morning hike, or dinner in town, let this map be your compass to wander well.

The region’s food scene reflects the creativity and community spirit of the Berkshires. Whether it’s a farm-to-table dinner, a casual morning coffee, or a local market visit, these spots capture the flavors of the area.

Guest favorites include The Cliff House (onsite), where lake views and seasonal ingredients set the tone for a thoughtful meal. A short drive away in Great Barrington, The Prairie Whale offers wood-fired fare and relaxed energy, while Hilltown Restaurant highlights regional produce in a charming countryside setting. For casual mornings, Marjoram + Roux and Cafe Holli are excellent picks for coffee and breakfast, and Guido’s Fresh Market is a staple for local goods and picnic provisions.

Art and culture run deep here. The Berkshires have long inspired artists and thinkers, and the region remains home to world-class institutions that invite exploration and reflection.

On the map, highlights include the Norman Rockwell Museum in Stockbridge, home to the artist’s original works and the Circle Museum in Austerlitz, NY, featuring striking metal sculptures in a pastoral setting.

Step outside and let the landscape guide you. Nearby parks, gardens, and hikes offer countless ways to reconnect with nature throughout the seasons.

For gentle wanders and scenic views, visit Berkshire Botanical Garden, French Park, or Jug End State Reserve, each offering its own quiet rhythm, from playgrounds and tennis courts to expansive garden paths. For hikes, favorites include Harvey Mountain State Forest, Flag Rock, and Brace Mountain, where wooded trails and ridgelines reward unhurried exploration.

Beyond food, culture, and trails, Prospect’s map highlights relaxed, characterful spots that offer a glimpse of local life.

In Great Barrington, Mooncloud is a cocktail and salumi bar with a refined yet unpretentious vibe, while Miller’s Pub is a warm spot to unwind after a day outdoors. Hy’s Fried pairs fried chicken with cocktails and dancing, and Bar Bene brings a cozy wine bar experience across the Hudson. For those interested in local cannabis culture, Devine Cannabis, Great Barrington Dispensary, and Rebelle all offer thoughtful, design-forward spaces.