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.

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!

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. 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.

Day 1 Itinerary

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

Head toward the train station to the meticulously curated, small, but mighty Brattleboro Museum and Art Center currently featuring powerful exhibits including Robert Visani: Form/Reform  and Yvette Molina: Big Bang Votive. 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 Shari 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. Also on Main is ZPots, featuring amazing works from Eric Hendrick and Noelle VanHendrick as well as a fantastic team of artisans.

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. On the first Friday of the month from May-December is Gallery Walk, where you can enjoy all the art the town has to offer.

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

Day 2 Itinerary

Head over to Amy’s Bakery Arts Cafe and enjoy some wonderful food, art, and a view of the Connecticut River. Amy’s has recently re-opened and we are so glad to welcome them back.

Looking to take in some live music? Check out the Brattleboro Music Center, Vermont Jazz Center, Epsilon Spires, or the Stone Church to see who is performing in town.

Maybe theater is your thing? See live theater at  the Hooker-Dunham, find a performance of the Vermont Theater Company, or see the best youth theater productions around at New England Youth Theater.

For dinner the River Garden Marketplace offers the best of both crafts – Beer and Art! With over 20 beers on tap as well as a dedicated craft marketplace for local artisans, it will satisfy all your cravings.

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 Itinerary

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.

Finally, treat yourself to some amazing food at Peter Havens. Coming into Peter Havens you will find a warm, welcoming bar where you can try one of our specialty cocktails. The modest dining room holds ten tables where you can have an intimate dinner for two or a celebratory party for ten or more friends and family.

Day 2 Itinerary

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. 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 Itinerary

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 Marlboro Road at Vermont Hempicurean, 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!). They focus on Farm to Body products and support the local hemp industry.

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. Stay right downtown at The Inn on Putney Road or The One Cat Bed and Breakfast.

Day 1 Itinerary

Start with a walk, run, or bike ride along the West River Trail. This beautiful, flat, trail starts in Brattleboro and continues along the West River to Dummerston and beyond. A perfect way to stretch your legs.

After your adventure, head for lunch at The Marina a classic restaurant (great vegetarian and vegan food available too) overlooking the mouth of the West and Connecticut Rivers, at the head of the trail.

Here in the winter? Try some downhill skiing at our own little hill at Living Memorial Park for just $5. Cross country more your speed? The town golf course transforms into 33 kilometers of cross country trails. Volunteer run by the Brattleboro Outing Club.

Hungry yet? Go downtown to Echo Restaurant downtown for delicious pasta, wood-fired pizza, and signature cocktails. If you find yourself here on a Thursday night in the summer, Retreat Farm has “Food Truck Roundup” with local food, beer, and music.

Stop into the Brattleboro Food Coop for snacks and supplies.

Day 2 Itinerary

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.

For dinner, get some dim sum to go at Cai’s Dim Sum in West Brattleboro, or head downtown and get some pizza, wings, burgers and more at Hazel (currently curbside only)

Day 3 Itinerary

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 authentic Thai food from High on Thai. You can eat in or find a spot at one of the outdoor parks around the Harmony Lot and on Main Street.

Every fall is Brattleboro Baconfest! Don’t miss all of this pork goodness.

Itinerary #4

Suggested for: Beer and Spirit Lovers

Vermont is home to hundreds of local craft breweries, wineries, and distilleries, many located right here in Brattleboro. Don’t miss your chance to taste some of the finest beverages around. Have a flight and sample all the different tastes. From IPAs to bourbon to wines of all kinds, Brattleboro has it all.

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 Itinerary

Enjoy the best of both crafts! Beer and Art! River Garden Marketplace is located right downtown. With its monthly rotating menu, 20 draft lines and over 50 bottles and cans, carefully curated from amazing breweries from Vermont and beyond, and the Curated by Hand Built Market, a rotating collection of artisans, craftspeople and artists from Vermont and our nearby neighbors, this is a great place to start your journey.

Head right across the the Marketplace up High Street and have a flight of sour beers at Hermit Thrush Brewery. The Brewery prides itself on fermenting since 2014 with only wild Brattleboro mixed culture yeast, continually pushing boundaries of new sour beer, and a brewhouse fueled by wood, not fossils. Like what you taste? Buy a 4-pack!

Walk some of that beer and food off with a visit to the Retreat Trails, Brattleboro’s urban forest. This expansive 10-mile trail network is within walking distance of downtown.

In the summer, be sure to try Saxtons River Distillery, offering tastings, food, and music outdoors. Try some Maple Liqueur, Maple Bourbon, or Snowdrop Gin.

Day 2 Itinerary

Ready for more? Start your day at Mocha Joe’s and enjoy a Red Eye Espresso, Nutty Vermonter Latte, or just a plain cup of coffee. They roast their own beans so be sure to pick up a pound to go.

Fill up with breakfast out in West Brattleboro at the Chelsea Royal Diner. Everything from homestyle pancakes to the “Royal Breakfast” it is a great way to start the day. Remember, breakfast is the most important meal of the day.

Travel over to Putney Road and visit Windham Wines. Windham Wines, brings the world of wine to Southern Vermont. The family-owned shop combines global selection and personal attention to help you find your next favorite bottle.

Drive a short ways farther down Putney Road and make a tasting appointment at Vermont Vermouth. They make craft vermouth in with a focus on sourcing local ingredients.

Annually in May, the town holds the Brattleboro Brewers Festival. This is year’s Festival is shaping out to be their best yet with up to 100 brews & ciders to sample along with some Vermont Wines and Spirits.

Day 3 Itinerary

Start your day at the Farmer’s Market  for homemade, homegrown, handcrafted food, vegetables, crafts, and music. Open every Saturday.

Explore Scott Farm Orchard. Scott Farm has been a working farm since 1791. They grow over 130 varieties of heirloom apples – many of which are used by local breweries and wineries.

End your visit on the roof of Whetstone Station for lunch, a pint, and a breathtaking view of the CT River. Whetstone proudly serves unique, small batch craft beers from our own breweries. With a wide variety of creative and award winning styles, we have a beer for every palate. Like what you taste? Take some home! Cans for sale right at the restaurant.

Itinerary #5

Suggested for: The Craft Curious

Since its earliest days, craft has been essential to survival in Wantastegok/Brattleboro VT and today its craft has become a way of life. Brattleboro has offerings that will keep the hand and mind busy and the senses enlivened as you explore the craft traditions that enrich our lives. Below, check out just one day’s worth of sensory activities as you sample craft culture at its finest.

One Day Itinerary

Get here in time for lunch at Top of the Hill Grill for some some savory down home smoked meats and hearty sides. Killer catfish to pulled pork wraps, take in the spectacular view of the West River meadows as you munch down on good old country cooking. End the meal with a signature chipotle brownie!

Head up the West River for an adventure of fire as you take in the world-class craftwork of glass artist Randi Solin and ceramicist Natalie Blake at Fire Arts Studios. Push your senses to the limit on a tour and demonstration; plan ahead to take a private class. Shop the Fire Arts gallery’s selection of fine craftwork from the region. While you’re there, stop in at the Fire Arts Café for a fresh-pulled espresso and a classic baguette to go.

With the sun at your back, enjoy the spectacular view of Mount Wantastegok as you head back toward town and stop at the Retreat Farm, home of Grafton Village Cheese and their unmatched collection of craft delicacies from around Vermont. If you’re lucky, the goats will be at play and local food trucks circled up. If you’re feeling the need for a little exercise, enjoy a walk among their 10-mile forest trail network.

Back in town, visit HatchSpace, downtown Brattleboro’s community woodworking studio. See novice and expert woodworkers using traditional and modern methods to make everything from bowls to benches, cutting boards to cabinets. Across the street, grab a pack of fine American sour ales crafted locally at the Hermit Thrush Brewery. Next head down to First Proof Press – our community print-making studio – to experience first hand the artistry of one of Brattleboro’s oldest industries.

Later, as you get some fresh air strolling Main Street, indulge yourself in the variety of craft traditions represented by Vermont Artisan Designs. Stop in at StationHaus to experience carefully curated rustic and chic design inspirations. Want to turn your own clay? Sign up in advance for a weekend clay class at the Wheelhouse Clay Center in Brattleboro’s Harmony Lot.

Begin winding down by easing into a crafted Turkish cocktail at the Tulip Cafe. Wrap up an exciting day with lite fare and a selection of Vermont’s finest craft beers at River Garden Marketplace – if you’re lucky you can catch the long rays of the setting sun glancing off the Connecticut River as you rest on their back patio to the tunes of a live jazz trio.

Where is Brattleboro VT?

We LOVE that you asked!
Easy as exit 1, 2 & 3 off I-91.

Hop a plane, take the train, or go for a drive!

Bordering the Connecticut River, Massachusetts, and New Hampshire, Brattleboro is easy to get to from New York City, Hartford, Boston, and Burlington, making it a perfect choice for a road-trip vacation.

Brattleboro is also accessible via Amtrak, with a station located in the heart of downtown Brattleboro, as well as from nearby airports including Bradley (Hartford) International Airport (74 miles), Albany International Airport (80 miles) and Boston-Logan Airport (117 miles).

Links we Love! Visit Brattleboro VT