The Berkshires' Best Bucket List
The Berkshires, with its stunning landscapes and vibrant culture, offer an abundance of experiences waiting to be discovered. Whether you’re a local looking to explore your own backyard or a visitor eager to dive into this picturesque region, our curated list of 100 must-do adventures will guide you through the best that the Berkshires have to offer. From thrilling outdoor activities to cultural gems, each item on this bucket list promises unforgettable memories and the chance to truly connect with the heart of the Berkshires. Get ready to embark on your next adventure!
✔️ Explore The Mount, the historic home of Edith Wharton, and stroll through its beautiful gardens.
✔️ Hike to the summit of Mount Greylock for breathtaking views and enjoy the view from the War Memorial.
✔️ Visit the Norman Rockwell Museum in Stockbridge to see original artwork and exhibitions.
✔️ Attend a performance at Tanglewood, particularly during the Boston Symphony Orchestra’s summer season.
✔️ Take a scenic drive along the Mohawk Trail, stopping at the various viewpoints and quaint towns.
✔️ Go skiing at Jiminy Peak Mountain Resort and ride the Alpine Slide in the summer.
✔️ Experience a cozy sleigh ride at Sweet Brook Farm, wrapped in blankets and pulled by horses.
✔️ Tour the Berkshire Museum in Pittsfield, exploring its art, history, and science exhibits.
✔️ Visit the Hancock Shaker Village to learn about Shaker craftsmanship and lifestyle.
✔️ Discover the history of the W.E.B. Du Bois Homesite and take a guided tour.
✔️ Take a stroll through the gardens at Naumkeag, particularly during the annual Festival of Flowers.
✔️ Enjoy a wine tasting at Hilltop Orchards, sampling local wines and ciders.
✔️ Kayak on the Housatonic River, taking in the scenic views and wildlife.
✔️ Explore the groomed trails at Notchview Reservation for cross-country skiing or snowshoeing.
✔️ Visit Chesterwood to see Daniel Chester French’s studio and beautiful grounds.
✔️ Go snowshoeing at Beartown State Forest and enjoy the tranquil winter landscape.
✔️ Enjoy a picnic at Lake Mansfield, especially in the summer months.
✔️ Browse the shops and galleries in Great Barrington for unique local art and gifts.
✔️ Explore the historic downtown of Pittsfield, stopping by local eateries and shops.
✔️ Take a guided tour of Ventfort Hall, a Gilded Age mansion with fascinating history.
✔️ Go ice skating at Berkshire School’s indoor rink during public skate sessions.
✔️ Hike the Appalachian Trail at Jug End and enjoy the natural beauty along the way.
✔️ Visit the picturesque town of Stockbridge and explore its quaint shops and eateries.
✔️ Experience contemporary art at Mass MoCA in North Adams, especially during special exhibits.
✔️ Attend a film screening at The Mahaiwe Performing Arts Center, enjoying its historic charm.
✔️ Discover hidden treasures at the Bidwell House Museum, learning about early American life.
✔️ Enjoy the scenic views from the summit of Mount Tom, especially during the fall.
✔️ Visit the Clark Art Institute in Williamstown to see its stunning art collection and gardens.
✔️ Take a relaxing dip in the Ashuwillticook Rail Trail during warmer months for biking or walking.
✔️ Participate in a local art workshop or class at one of the many galleries.
✔️ Go fishing at Goose Pond or one of the many lakes in the area for a peaceful day outdoors.
✔️ Attend the annual Lee Founders Day Festival with family-friendly activities and local vendors.
✔️ Explore the Berkshire Athenaeum for its historic architecture and local history collections.
✔️ Enjoy a delicious dinner at Gedney Farms, featuring locally sourced and seasonally inspired foods.
✔️ Discover the beauty of Bartholomew’s Cobble, perfect for hiking and nature walks.
✔️ Visit the historic Red Lion Inn for its charm and delicious dining options.
✔️ Go mountain biking on the trails at Pittsfield State Forest during the warmer months.
✔️ Attend the Great Barrington Farmers Market for local produce and handmade goods.
✔️ Explore the grounds at the Massachusetts Museum of Contemporary Art during the summer.
✔️ Take a scenic train ride on the Berkshire Scenic Railway, enjoying the views along the way.
✔️ Visit the historic site of Fort Massachusetts, exploring its role in local history.
✔️ Walk the charming streets of Lenox, stopping for tea at a local café.
✔️ Experience the thrill of zip-lining at Jiminy Peak and enjoy the views from above.
✔️ Relax with a spa day at Canyon Ranch in Lenox for a rejuvenating experience.
✔️ Try your hand at plein air painting at one of the region's scenic overlooks.
✔️ Attend the Berkshire International Film Festival in Great Barrington for independent films.
✔️ Visit the Haywood Estate in Great Barrington, a historic gem with beautiful grounds.