Brattleboro
Day Plans

Make the most of your day with our curated plans, packed with Brattleboro's hidden gems and unique experiences!

day 1

Brattleboro Bliss

morning

:

Start your day with a leisurely breakfast at a local café. Enjoy a stroll along the Connecticut River for breathtaking views.

afternoon

:

Visit the Brattleboro Museum & Art Center to appreciate local artworks. Afterward, explore unique shops and boutiques downtown.

evening

:

Dine at a quaint restaurant known for its farm-to-table offerings. Wind down with live music at a nearby venue.

day 2

Nature Explorer

morning

:

Hike at the nearby Wantastiquet Mountain for panoramic views. Feel the fresh air and connect with nature on this exhilarating trail.

afternoon

:

Grab lunch in Brattleboro, then head over to the retreat area for meditation or relaxation. Embrace the tranquility of the surroundings.

evening

:

Watch the sunset from a scenic overlook. Enjoy dinner with friends at a local pub and share stories of the day’s adventures.

day 3

Art & Culture Day

morning

:

Start with a coffee at a local café, then visit the Brattleboro Film Festival if it's the right season. Engage with filmmakers and enjoy thought-provoking films.

afternoon

:

Explore the local art galleries showcasing the works of regional artists. Participate in workshops that might be available.

evening

:

End your day with a cozy nightcap at a local bar. Reflect on the inspiring art you experienced during the day.

day 4

Rustic Retreat

morning

:

Savor breakfast at a local diner, then head to the West River Trail for a refreshing walk. Enjoy the scenic beauty alongside the river.

afternoon

:

Visit local farms and markets to buy fresh produce and artisan goods. Engage with farmers and learn about sustainable practices.

evening

:

Cook your bounty from the market for dinner. Share a meal with friends around a warm fire, surrounded by nature.

day 5

Culinary Journey

morning

:

Start at a local bakery for fresh pastries and coffee. Consider joining a morning cooking class for a fun hands-on experience.

afternoon

:

Visit a community kitchen where you can learn about local ingredients. Enjoy tasting sessions featuring the region's culinary delights.

evening

:

Attend a gourmet dinner hosted by a local chef. Appreciate the culinary art while mingling with fellow food lovers.

day 6

Active Adventures

morning

:

Rent a bike and explore the bike paths in town. Experience the beautiful landscapes while getting some exercise.

afternoon

:

Stop at a local café for lunch and a refreshing drink. Afterwards, continue your ride to explore surrounding attractions.

evening

:

Relax with a casual dinner at a burger joint. Enjoy the laid-back atmosphere and chat with fellow bikers about your adventures.

day 7

Urban Exploration

morning

:

Enjoy breakfast at a trendy brunch spot in town, then hit the downtown shops. Explore bookstores and artisan vendors for unique finds.

afternoon

:

Visit the historical sites and learn about the area’s rich history. Stop by the local library for any interesting exhibitions.

evening

:

Choose a dinner spot that offers international cuisine. Conclude the day with a stroll along the lively streets enjoying the night ambiance.

day 8

Music and More

morning

:

Start your day with breakfast while listening to local musicians at a café. Absorb the creative vibe of the town.

afternoon

:

Visit the local record shop and discover new artists. Engage in a drum circle or dance workshop if available.

evening

:

Attend a concert at a local venue featuring regional artists. Enjoy a night filled with rhythm and enjoy some local brews.

day 9

Wellness Escape

morning

:

Join a yoga class at a local studio to start your day centered. Follow it with a healthy breakfast smoothie at a juice bar.

afternoon

:

Visit a nearby spa for an afternoon of relaxation and treatments. Treat yourself to a massage or facial.

evening

:

Enjoy a light dinner at a health-focused restaurant. Spend the evening meditating or reading by a calming fireplace.

day 10

Stargazer's Night

morning

:

Visit a local café for a hearty breakfast. Spend the morning visiting the local observatory to learn about stargazing.

afternoon

:

Explore the local region’s natural beauty through a hike. Collect some photos to document your love for nature.

evening

:

Set up a stargazing spot at a quiet area with minimal light pollution. Enjoy hot cocoa and share the beauty of the night sky with friends.

Discover Brattleboro

Read more in our Brattleboro 2024 Travel Guide.

Brattleboro Travel Guide