Things to Do in Brattleboro, Vermont: A Local’s Guide to the Best Spots
Greetings from Brattleboro!
Some links in this post are affiliate links, meaning I will earn a commission (at no extra cost to you) if you click through and make a purchase. For more info, please see my disclaimer.
Brattleboro, or Bratt as us locals affectionately call it, is where I spent much of my youth. I grew up outside of Bratt in an even smaller town, and until I traveled to Boston as a middle schooler, Bratt and nearby Keene were my ideas of a city. Compared to my sleepy hometown, Bratt had it all: shops, restaurants, grocery stores, and not one but two movie theaters. It filled child-me with awe. I loved going there, and while some things about the town have changed in the intervening years (the closure of one of the theaters, for instance), my love for it has not. I love this corner of southern Vermont, and I can’t wait to tell you about some of the amazing things to see and do here.
1. Explore Downtown Bratt
Brattleboro’s downtown area is fairly compact, making it perfect to explore on foot. Park on Main Street (or if parallel parking ain’t your thing, there’s Harmony Parking Lot off of Elliot Street or Preston Lot off of Flat Street) and peruse the many shops lining Main Street and Elliot Street. Two of my favorite stores are Brattleboro Books, a well-stocked used bookstore, and Penelope Wurr, a beautifully curated shop filled with unique gifts and knick-knacks as well as British specialty products (Flake bar, anyone?). Also, if you’re an audiophile, be sure to pop into Turn It Up! and check out their collection of vinyl and CDs.
2. Delight Your Taste Buds with Lunch at Yalla
Yalla makes the best falafel and pita I’ve ever had (and I’ve had my fair share). Their pita is light and pillowy, and their falafel, which is always piping hot (the place is so popular that the falafel is never sitting out for long), is flavorful and fried to perfection. My go-to order is the Yalla Sababa with a half pita and all of the fixings, except for the boiled egg; it is simply divine (my mouth is watering just thinking about it).
Please note that Yalla is only open for limited hours (currently, Thursday through Sunday from 11:00am – 3:00pm), and the restaurant closes entirely during March and April. It is also extremely popular; lines out the door are not uncommon.
3. Enjoy Vegan Fare at Superfresh! Organic Café
If you’re not in the mood for falafel, another great option is Superfresh!, which, in addition to being entirely vegan and organic, is both gluten-free and soy-free. Their food is freshly made and bursting with flavor; it’s good food that you can feel good about eating. In case that is not incentive enough to eat here, the café itself is super cozy, with colorful walls and large windows that bathe the space in light.
Similar to Yalla, Superfresh! has limited hours. At present, it is only open Friday through Monday from 12:00pm – 6:00pm.
The Yalla Sababa from Yalla
4. Sample the Best Mac and Cheese around at Vermont Country Deli
Here’s another food option for you: Vermont Country Deli. Open every day from 8:00am to 6:00pm, this Brattleboro staple is a great choice for breakfast or lunch – or even an early dinner. Their must-try menu item is the skillet-baked mac and cheese. It’s ooey gooey with just the right amount of sharpness, and it has a devoted, far-reaching fan base. I once met someone who, upon hearing that I was from the Brattleboro area, exclaimed, “The place with the best mac and cheese ever.” True story.
Their desserts, especially their face-sized cookies, are also top-notch, as are their sandwiches. And they are conveniently located along two major roadways: Route 9 and Interstate 91.
5. Satisfy Your Sweet Tooth at Tavernier Chocolates
Opening its Main Street shop in 2024, Tavernier Chocolates is a relatively new addition to downtown Bratt, though it has been in operation and selling its chocolates since 2014. Its new storefront is cozy and inviting, with a myriad of confectionery creations and local products on display. From decadent white chocolate topped with dried berries to the ever-classic dark chocolate with sea salt, the flavor options are varied, but no matter the ingredients, they all share one key feature: tempering. All of the chocolates are beautifully tempered, giving them a gorgeous sheen and texture.
My all-time favorite chocolate of theirs is the maple sugar log: dark chocolate “logs” filled with caramelized maple sugar. Their drinking chocolate is also not to be missed (I always keep my pantry stocked with at least one bag of it).
6. Get Your Caffeine Fix at Mocha Joe’s or Duchess Coffee
Brattleboro punches above its weight when it comes to coffee. The town is home to not one but two artisanal coffee roasters: Mocha Joe’s and Duchess Coffee. The former, a veritable landmark on Main Street, has been roasting and brewing coffee since 1991, and the space has retained its unpretentious 90s décor. You’ll come for the coffee, but keep coming back for the vibe. My go-to Mocha Joe’s drink is the iced chocolate monkey with oat milk and a shot of espresso – yum!
Duchess Coffee, having opened its doors in 2021, is the new kid on the block, but it is in no way inferior to Mocha Joe’s. Its coffee, which is roasted in small batches, is some of the best that I’ve ever had. Plus, Duchess is women-owned and sources its coffee beans from women-owned farms in Central and South America. I almost forgot to mention – Duchess Coffee is also part bookshop, containing a curated selection of books from Antidote Books. My go-to Duchess drink is the iced Duchess grey latte with oat milk.
Cozy interior of Duchess Coffee
7. Hike Mount Wantastiquet
Now, technically, Mount Wantastiquet is not in Brattleboro, or even Vermont; it’s across the Connecticut River in New Hampshire. And when I say across the river, I mean literally across the river: from downtown Bratt, you cross the bridge into New Hampshire, turn left onto Mountain Road, and then, keep driving until you come to the trailhead parking lot. The trail up to the summit is not too bad; it took me about an hour last time I did it. The hike, however, is pretty much all uphill, with around 1,000 feet in elevation gain, but the view from the top is worth the effort.
Be sure to wear proper footwear (my current hiking shoes are the Alpaca Breeze Low from Hoka) and bring food and water to stay hydrated and fueled (Nalgene is my go-to water bottle for hiking).
8. Rent a Canoe or Kayak and Paddle up the West River
If hiking ain’t your thing, you can still bask in the area’s natural beauty by renting a canoe or kayak at Vermont Canoe Touring Center. I highly recommend steering to the right when you leave the docks and canoeing (or kayaking) in the West River. The first section of the West River is known as the Retreat Meadows (or simply, “the Meadows”), and it is where the West River meets the Connecticut River. The water here is calm, making it an ideal spot for beginners. If you have prior canoeing and/or kayaking experience, you can paddle through the Meadows and up part of the West River.
I do not recommend canoeing or kayaking in the Connecticut River (i.e., going left and under the bridge). It is a larger, busier river, and it is not uncommon for boaters to go speeding up it, creating sizable wakes that can easily capsize your kayak or canoe if you aren’t careful.
Please note that your canoe or kayak rental includes paddle(s) and life jacket(s), but it does not include a dry bag to store your personal items (e.g., car keys and phone) while out on the water. I recommend bringing one with you; I own and use this 10L dry bag.
9. Catch a Movie at the Historic Latchis Theatre
Opened in 1938, the Latchis Theatre boasts stunning Art Deco architecture as well as gorgeous Greek murals, including one of the Zodiac constellations that spans the entirety of the main theater’s ceiling. Growing up, I took the beauty of this historic theater for granted, but that all changed when I moved to Boston and went to a chain theater for the first time.
Paddling back after a couple of hours out on the West River
10. Bowl a Strike at Brattleboro Bowl
I sincerely hope that Brattleboro Bowl never renovates because a large part of its charm is that it looks exactly the same as it did when I started going there as a kid. Another reason to love it: it has old-school bowling without any string pins. So, if you’re like me and find the sound of pins being knocked over cathartic, you’re in luck. And if you find yourself in Bratt on a Friday or Saturday night, head here for their Cosmic Bowling featuring colorful lights and cranked-up music.
11. Drive up Hogback Mountain
As with Mount Wantastiquet, Hogback Mountain is not actually in Brattleboro; it is in Marlboro, a 20ish-minute drive from Bratt. The panoramic views from the lookout, however, are well worth the drive, especially in the fall during peak foliage. I do not recommend driving up here in the winter, though, as the mountain road can become quite treacherous due to snow and/or black ice.
12. Savor Local Produce and Gorgeous Views at Green Mountain Orchards
Also not in Bratt but well worth the visit is Green Mountain Orchards. Open from mid-July to Christmas, this Putney-based orchard offers seasonal pick-your-own blueberries, apples, peaches, raspberries, pumpkins, and plums. They also sell a whole host of local products, including Vermont maple syrup, as well as their own baked goods. If you come during the autumn, you must try their apple cider donuts – they are to-die-for.
Ambling through the rows of apple trees at Green Mountain Orchards
13. Treat Yourself to a Fancy Dinner at TJ Buckley’s
Tucked away in a restored 1925 dining car, TJ Buckley’s is a hidden gem. Its unassuming exterior belies the world-class cuisine within. With an emphasis on local, seasonal ingredients, Chef-Owner Michael Fuller crafts an ever-changing menu of tantalizing appetizers, entrées, and desserts. The food, however, is but one half of the restaurant’s appeal; the other is the intimate dining experience. With only eight tables and an open, single-stove kitchen, TJ Buckley’s feels more akin to eating at someone’s house than a restaurant, and that makes for a truly unforgettable experience.
TJ Buckley’s is only open for dinner Thursday through Sunday, and I highly recommend calling ahead to make a reservation.
14. Honorable Mentions (a.k.a., Places and Events I Have Heard Good Things about but Have Yet to Visit or Attend)
In no particular order, these are Gallery Walk/Brattleboro First Fridays, Brattleboro Museum and Art Center, and Brattleboro Area Farmers’ Market.
And that does it for this list. I hope you have a wonderful time in Brattleboro, and if you have any questions, please feel free to ask them in the comments section below!
-Julia
P.S. If you enjoyed this post, please consider supporting me on Buy Me a Coffee.
