5-day Trip to Greenfield, Massachusetts Itinerary

Start your day with a refreshing hike at the Mount Sugarloaf State Reservation. Enjoy the scenic views from the summit and take in the natural beauty of the area. Afterward, grab a quick snack at The Roost, a local cafe known for its pastries and coffee.

Explore the Green River Swimming and Recreation Area for a relaxing afternoon by the river. Pack a picnic lunch and enjoy the peaceful surroundings. If you're feeling adventurous, try tubing or kayaking in the river. For dinner, head to The People's Pint for another delicious farm-to-table meal.

End your day with a visit to The Arts Block, a historic building that hosts live music, theater performances, and art exhibitions. Enjoy a drink at their bar and soak in the lively atmosphere.

Take a day trip to the nearby city of Northampton. Start your day with a leisurely walk along Main Street, known for its unique shops, boutiques, and art galleries. Stop by Bread Euphoria for a delicious freshly baked pastry and a cup of coffee.

Visit the Smith College Museum of Art to admire its impressive collection of artworks from around the world. Take a break for lunch at Pizza Paradiso, a local pizzeria known for its wood-fired pizzas and cozy atmosphere.

Explore the vibrant nightlife of Northampton by visiting The Iron Horse Music Hall, a renowned music venue that hosts live performances by local and national artists. Grab dinner at Northampton Brewery, a popular brewpub serving tasty pub fare and a wide selection of craft beers.

Take a scenic drive to the charming town of Brattleboro, Vermont. Start your day with a visit to the Brattleboro Farmers' Market, where you can find fresh local produce, artisanal products, and handmade crafts. Grab a coffee and a pastry at Mocha Joe's, a local coffee shop.

Explore the Retreat Farm, a working farm and educational center. Take a guided tour, interact with farm animals, and learn about sustainable agriculture. Enjoy a picnic lunch at the farm or try Whetstone Station Restaurant and Brewery, a riverside brewery and restaurant known for its craft beers and delicious food.

Stroll along Main Street in downtown Brattleboro and explore the unique shops, art galleries, and antique stores. For dinner, try Peter Havens, a cozy restaurant offering French-inspired cuisine made with locally sourced ingredients.

Visit the Greenfield Public Library and spend some time exploring their collection of books, magazines, and local history resources. Grab a coffee and a pastry at The Roost before heading to the Greenfield Energy Park, a community space that hosts events and exhibitions related to sustainable energy and environmental awareness.

Discover the local art scene by visiting Greenfield Gallery, a contemporary art gallery showcasing works by local and regional artists. For lunch, try The Brass Buckle for their creative sandwiches and salads.

Enjoy a relaxing evening at The People's Pint, a local brewery and pub known for its craft beers and friendly atmosphere. Pair your drink with some delicious pub food and unwind after a day of exploration.