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 Dosa Kitchen for some inspired “Indian street-food” that almost looks too pretty to eat. Don’t forget to buy their cookbook on the way out – you’ll want to make the sauces at home. Take the stairway at the municipal parking garage to Vermont Center of Photography’s 2020 Open Juried Exhibition through August 30 (please call ahead to make an appointment).

Head toward the train station to the meticulously curated, small, but mighty Brattleboro Museum and Art Center currently featuring six powerful exhibits including Alison Wright: Grit and Grace, Women at Work. 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 Backlot Cinema at Epsilon Spires featuring eclectic film themes such as Afro-futurist Sci-Fi and Muscle Beach in the 70’s. The outdoor, social distance-friendly venue will have a bar and food available.

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 an authentic Thai foot massage at luxuriously appointed Thai Sabai.

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 morning Detox + Glow treatment at the studio of Senja Curran which is “dedicated to providing a sanctuary where clients feel safe, held, and cared for.” Open by appointment.

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 Top of the Hill Grill barbecue restaurant (great vegetarian and vegan food available too) to get your bearings at 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 across the road to enjoy dinner alfresco overlooking the Retreat Meadows waterway at the Marina.

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 (11 am – 2 pm / 10 am to 11 am reserved for high-risk shoppers) to jam on live music, 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

Hit up adorable Cooper’s Coop on Western Ave, or at your Airbnb, cook up the goodies you got the day before at the Farmer’s Market.

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 Yala Vermont. You can eat in or find a spot at one of the outdoor parklets around the Harmony Lot and on Main Street.

Call for a take-out growler from McNeill’s Brewery 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

Park at the town garage on Elliot Street and arrive in time for lunch at Dosa Kitchen for some inspired “Indian street-food.” Don’t forget to buy their cookbook on the way out – you’ll want to make the sauces at home.

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.

Next door, on Flat Street proper pick up a surprising mix of fun and healthy supplies at Dottie’s Discount Foods (child of the Brattleboro Food Coop).

Go for inside or back patio cocktails and dinner at Echo on Main Street before heading to awesome Backlot Cinema at Epsilon Spires featuring film themes such as Afro-futurist Sci-Fi and Musclebeach in the 10’s. The outdoor, socially distance-friendly venue will have a bar and food for snacks and bevs.

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.