5-day trip to Greenfield, MA Itinerary

Start your day with a hike at the Poet's Seat Tower. Enjoy panoramic views of the surrounding area from the top of the tower. After the hike, grab a quick snack at The Hub, a local cafe known for its delicious pastries and coffee.

Head to the Deerfield River for an afternoon of kayaking or tubing. Rent equipment from Zoar Outdoor and enjoy a leisurely paddle down the river. After your water adventure, have a late lunch at The Wagon Wheel, a classic American diner with a wide range of comfort food options.

Relax and unwind at The People's Pint with a refreshing craft beer and some tasty appetizers. Enjoy the laid-back atmosphere and chat with the friendly locals.

Start your day with a visit to the Greenfield Public Library. Explore the library's extensive collection and relax in the cozy reading area. Afterward, grab a coffee and a pastry at The Roost, a charming coffee shop located nearby.

For lunch, try The Brass Buckle again, this time for their delicious sandwiches and salads. After lunch, visit the Greenfield Center School, a progressive school that offers a unique educational experience. Take a tour of the campus and learn about their innovative teaching methods.

Enjoy a dinner at The People's Pint and try their famous beer-battered fish and chips. After dinner, catch a movie at the Greenfield Garden Cinemas, a local cinema that screens a mix of mainstream and independent films.

Take a day trip to nearby Northampton, Massachusetts. Start your day with a leisurely breakfast at The Roost. After breakfast, explore the vibrant downtown area and visit the Smith College Museum of Art to admire its impressive collection of artwork.

For lunch, head to Pizza Paradiso, a popular pizzeria known for its delicious wood-fired pizzas. After lunch, take a walk along the Connecticut River Greenway and enjoy the scenic views of the river.

Have a relaxing dinner at Paddy's Pub, a cozy Irish pub with a welcoming atmosphere. After dinner, explore the local music scene by catching a live performance at The Iron Horse Music Hall, a renowned music venue in Northampton.

Take a day trip to Brattleboro, Vermont. Start your day with a hearty breakfast at The Works Bakery Cafe. After breakfast, explore the charming downtown area and visit the Brattleboro Museum & Art Center to experience the local art scene.

For lunch, try Whetstone Station Restaurant and Brewery, a waterfront restaurant that offers a variety of delicious dishes and craft beers. After lunch, take a stroll along the Brattleboro Retreat Trails and enjoy the peaceful nature surroundings.

Enjoy a dinner at Twilight Tea Lounge, a unique restaurant that specializes in vegetarian and vegan cuisine. After dinner, relax with a cup of tea and enjoy the cozy ambiance of the tea lounge.