Love Brattleboro VT Itineraries

There are so many things to love about Brattleboro that there is no way to get it all in on one visit. Before you come, stock up on masks to comply with the state mandate to wear them. Also, please check current travel restrictions and requirements on the Vermont Health website.

Below we offer suggested itineraries to get you started. You can do them in a half-day, full-day, or weekend. And while we’ve divided them up by lifestyle, some of the best trips are a mash up. Brattleboro’s offerings are as interesting and complex as you are!

While we’ve done our best to represent what’s open on these days, understand that in these shifting times, please call to confirm anything that you don’t want to miss. Plus, we are confident that you can find tons of other amazing things that are not listed here by just walking around. Other great resources are the Downtown Brattleboro Alliance and the Brattleboro Area Chamber of Commerce.

Itinerary #1


Heart-achingly picturesque Brattleboro VT is home to over 1000 arts and cultural events in a typical year, so you can’t help but fall in love with the town again and again. But even in this atypical year, Brattleboro has day, stay, and play offerings as interesting and complex as you are. Below, check out just one day’s worth of arts-intensive activities.

One-Day Itinerary

Get here in time for lunch at Yalla for some inspired, local, Middle Eastern food including hummus, tahini, pita, skhug, and many salads and amazing pita sandwiches. Don’t forget to buy their hummus on the way out!

Head toward the train station to the meticulously curated, small, but mighty Brattleboro Museum and Art Center currently featuring six powerful exhibits including William Ransom: Keep Up/Hold Up. Then, make your way up Main Street to River Gallery School of Art for an ever-changing display of student work and a gallery of portraits of local influencers and business owners, or plan ahead to take a class or workshop.

Pop around the corner on Elliott Street to check out the Harmony Collective local artist co-op for one-of-a-kind finds. Continue through the Harmony parking lot to Wheelhouse Clay Center, established by local pottery icons Teta Hilsdon and Grace Zabriskie for hands-on 3rd Friday “Clay and Play” and date night events, and shop some of the finest local ceramics.

Pop out the High Street side of the Harmony lot and cross Main to Mitchell Giddings Fine Arts owned and operated by local artists Petria Mitchell and Jim Giddings, featuring their work along with a dazzling artworks by an array of recognized fine artists.

By now you will be starving. Head back across the street to enjoy inspired, fresh farm-to-table fare and cocktails at Duo on the corner of High and Main Streets. To top off your perfect Brattleboro Friday night, walk a half block to Epsilon Spires featuring eclectic programming with film themes such as Afro-futurist Sci-Fi and Muscle Beach in the 70’s or free organ concerts!

Finally, if you can stay overnight (and frankly, we think you won’t want to go home), spend the night at the iconic art deco Latchis Hotel.

Itinerary #2

Suggested for: Self-Care Seekers

When you enter the space around Brattleboro you can’t help but feel the healing energy as the American and African tectonic plates converge in the middle of the Connecticut River with the confluence of the West River. (The traditional name for the West River is Wantastiqet – meaning a place where things are lost, and a place where things are found.) The air is so clean here that you can pick out individual scents of trees, wildflowers, rocks, and the water. And the light is stop-in-your-tracks delicious. This place call to you to slow down and take care of your person, breathe in the power of reflection, strength, and love. Here are just a few places for you to indulge in your good health.

Where to Stay

Setu for a health and wellness retreat package, or book their AirBNB space.

Day 1:

Pop into the Brattleboro Food Coop on the way into town for all of your healthy snack and Kombucha needs (if you are a dairy person, the cheese tastings are out of this world! We all need our calcium, right?)

Call ahead to make an afternoon appointment for a relaxing facial with Mary at Advanced Skin Care.

Continue your pampering with an adorable haircut, or waxing with the attentive team at Salon Jacque.

Ancient nutritious Mayan recipes have been handed down over generations to the family that will make dinner for you at Three Stones restaurant. Homemade tortillas and vegan options are on the traditional menu. Be sure to make a reservation because this intimate space fills up quickly.

Day 2:

You will wake to a fresh, healthy breakfast at Setu to start your day off right.

After morning Yoga sessions, head into Brattleboro and grab lunch from 100% vegetarian Superfresh! Organic Café. The food is not just uber healthful, it is also beautiful. The café is currently curbside pick-up only, but you an find a relaxing spot at one of the many fresh air dining parklets around town. Oh, and when you place your order, be sure to include their cookbook Healing Tonics, Juices, and Smoothies.

After lunch, head to your pre-booked healing session with Jasmine Healing Arts. You can choose from a menu of spa treatment, but we recommend a Crystal Chakra Balancing session to restore a healthy energy field through the focused power of crystals, and including a reiki session to nourish mind, body, and spirit.

Now that you know your crystals, make your way to Cara Wolff Jewelry, where designs include careful selections of vibrant and powerful gemstones. The shop also features locally harvested mushroom tinctures by Dark Matter, and organic cold-brew coffee that can be sipped in a nook overlooking the heart of downtown Brattleboro.

Your energy cleansing and shopping will likely make you famished. Stop in to India Masala House where you can continue your journey with a cuisine rich in spices for flavor and health, while capturing the essence of culture. Dining is available indoor or on the garden patio.

Day 3:

Continue the last day of your self-care ritual with a Face Reading at the studio of Diedre Kelley Face Reading is an ancient technique based in Classical Chinese Medicine and Daoist philosophy that helps people to better understand their gifts and talents through face shape and other unique qualities on the face.

Follow your treatment with a nutrition-packed quinoa bowl or a smoothie made with fresh fruits and vegetables from The Works where all food is made inhouse from scratch from ingredients that are created without the use of pesticides, hormones, or antibiotics.

Finally, natural healing remedies await you on Putney Road at Ceres Natural Remedies, offering a large selection of natural hemp-based CBD products. The folks there will be happy to walk you through plant-based wellness options for you (and your pets too!).

Bonus: If you can’t make it to Brattleboro, or if you want more when you leave, check out BodhiFit Yoga which offers inspiring sessions online.

Itinerary #3

Suggested for: Outdoor Enthusiasts & Foodies

Let’s face it, food always tastes better after a jaunt into the outdoors. Brattleboro has the perfect combination of stunning outdoor locations and activities for folks at every level, and amazing food created by local artisans to feed the hunger that follows, or niggles along the way. This itinerary is intended for folks who want to embrace the water or landscape, stop to smell the sustenance – or do both at the same time.

Where to Stay

Brattleboro has a number of charming inns and hotels. Check out the options at the Brattleboro Chamber website or explore AirBNB.

Day 1: Friday

Arrive in time for lunch at The Marina a classic restaurant (great vegetarian and vegan food available too) overlooking the mouth of the West and Connecticut Rivers.

Travel a few thousand feet down Putney Road and rent a canoe at the Vermont Canoe Touring Center to spend the afternoon paddling the lush CT and West Rivers.

Return your canoe and head to Echo Restaurant downtown for delicious pasta and signature cocktails.

Stop into the Brattleboro Food Coop for snacks and supplies.

Day 2: Saturday

Pick up some of astounding array of fresh favorites from Vermont Country Deli on Western Ave west of I-91.

Head down the road to the Brattleboro Farmer’s Market (every Saturday 10 am – 2 pm) to find real farmers, shop for sundry local fresh and handmade items. Check here for a list of current vendors. Be sure to grab snacks for your afternoon hike.

Head out of downtown a few minutes to hike Round Mountain Trail. The lower trail is a lovely open-field workout on its own, but it’s worth it to climb all the way to the top for the stunning view if you have time. Then, head up the road a bit and stop at Robb Family Farm for all things Maple.

Make reservations for dinner on the deck or inside at Peter Havens to experience the freshest local ingredients and inspired farm-to-table fare.

Day 3: Sunday

Head downtown and shop the beguiling, chock-full maze of upper, lower, and around-the-corner rooms at Sam’s Outdoor Outfitters.

Lunch up with Middle Eastern vegetarian takeout from High on Thai. You can eat in or find a spot at one of the outdoor parklets around the Harmony Lot and on Main Street.

Pick up a 4-pack from the Sour Beer only brewery Hermit Thrush as you head out of town.

Itinerary #4

Suggested for: Urban Adventurers & Arts Aficionados

By now you should know that Brattleboro is a mecca for artists. And by “artists” we mean all kinds of artists: Painters, potters, musicians, dancers, film makers, circus artists, jewelry makers, culinary artisans. Many of these folks have been here from birth or soon after. But many intentionally relocated bringing some of their artist city smarts and urban adventurer expectations with them. This itinerary is intended to showcase the degree to which arts and culture are a part of the community and some of the amenities that support and inspire them.

Where to Stay

Latchis Hotel “Dinner & A Movie” package, or explore AirBNB stays for unique Brattleboro properties like this Charming Studio in 19th Century Church.

Day 1: Friday

Get here in time for lunch at Yalla for some inspired, local, Middle Eastern food including hummus, tahini, pita, skhug, and many salads and amazing pita sandwiches. Don’t forget to buy their hummus on the way out!

Head across the street to Everyone’s Books (“Raising hell since 1984”) for some peoples-centric reads and fabulous cards. Take the stairway at the town parking garage down to Flat Street for some serendipitous finds at Experienced Goods Thrift Shop supporting Brattleboro Area Hospice.

Go for inside or back patio cocktails and dinner at Echo on Main Street.

Day 2: Saturday

Get your healthy and fortifying breakfast on at The Works Café.

Head toward the train station to the meticulously curated, small but mighty Brattleboro Museum and Art Center.

Pop over to Elliot Street Fish and Chips for a not-your-usual twist on this New England Favorite. Then, head up Main to Mitchell Giddings Fine Arts.

If you can stand to look at more beautiful works of art, pop into Gallery in the Woods and don’t miss the downstairs which tends of have surprising installations.

End your afternoon of browsing and shopping at Beadniks which is part arts and crafts store, and part fascinating historical bead museum (head downstairs for that too).

Call for reservations for a refreshing and fulfilling Italian dinner at Blue Moose Bistro as a part of your Dinner & A Movie Latchis Hotel package.

Finally, be sure not to miss the opportunity to see a movie at the historic Latchis Theatre, part of the non-profit Latchis Arts group. The popcorn and sodas are included as a part of your hotel package!

Day 3: Sunday

Start your day with a fresh farm to table inspired brunch at Duo.

Stop into Hermit Thrush Brewery across High Street to pick out a fun six pack of sour beer to take home with you.

Head back down Mainstreet and stop into Vermont Artisan Designs for a sampling of fine local arts and don’t miss the upstairs galleries.

Slip around the corner to check out Boomerang’s well-curated hipster collection of new, used and vintage apparel and sundries.

Head back down the hill on Mainstreet to Twice Upon a Time where untold antique treasures and ephemera abound.

End your visit on the roof of Whetstone Station for lunch, a pint, and a breathtaking view of the CT River.