9 Romantic Things to Do in Brattleboro VT: Be Jungle Book Adjacent

How can you resist a small town that once decided to make fun of Spain’s Running of the Bulls with its own chill, groovy, Vermont take: “Strolling of the Heifers?” Although that event doesn’t take place anymore, it proves that Brattleboro VT, in Southern Vermont, can be just the sort of fun-poking place ripe for exploring.

You’ll find a mind blowing place to stay – at the Vermont home of one of the world’s most famous 19th-century authors. You’ll also discover performing arts and culture, art galleries and museums, craft beer (although sadly, Hermit Thrush Brewery has closed), the Brattleboro Area Farmers Market, and more at this town on the confluence of the Connecticut and West Rivers.

Downtown Brattleboro VT

For lodging, we chose a revived inn, once hot, then not, now hot again, about 10 miles away in Newfane. Want to hit other hot spots in Brattleboro VT? Read on.

(For more dreamy escapes in Vermont – check out this Mavens Best Romantic Getaways in VT post)

Where Is Brattleboro Vermont?

Nestled in the southeastern corner of Vermont, Brattleboro is an inviting town with a strategic location near the borders of Massachusetts and New Hampshire. This charming town is situated along the banks of the Connecticut River, offering stunning vistas of the surrounding hills and valleys. Its proximity to major cities like Boston, Massachusetts, and Hartford, Connecticut, makes it easily accessible for travelers seeking a quintessential Vermont experience.

Things to Do in Brattleboro VT

TASTE: Putney Mountain Winery – Putney

Located in the very touristy Basketville about 12 miles north of Brattleboro (how can you miss those billboards on I-91?), you’ll find the Putney Mountain Winery, owned by local couple Kate and Charles Dodge.

Sure, you can go nuts buying baskets of every sort. But walk to the rear of this massive store and try some decent dessert wines and liqueurs. It’s all made in the back room – incredibly, a Mom and Pop operation inside a tourist spot.

Brattleboro Museum of Art Center, Brattleboro VT

VISIT: Brattleboro Museum Art Center

You’ll find something new each time you come to this non-collecting contemporary art museum within a repurposed train station. Brattleboro Museum Art Center displays art of all kinds; fine, video, and performance – as it pertains to contemporary art. And it promotes artists on the fringes as well.

Outsider, visionary, and “artists on the autism spectrum” are all featured here. Exhibits change three or four times a year, so there’s always something new to see.

LISTEN: Vermont Jazz Center

The leading Jazz venue in New England, the Vermont Jazz Center‘s mission is threefold. To “present world class jazz concerts,” provide educational workshops and other opportunities, and community outreach. So, if you’re in town on a concert evening, definitely go.

GO/LISTEN: Estey Organ Museum

So, those who know me understand that I get all geeky when it comes to obscure attractions, and the Estey Organ Museum surly is one. From the late 1800s through the 1950s, the name Estey was known worldwide for the manufacturing of its reed, pump, and electronic organs – and all were made in this little town of Brattleboro VT.

Though the museum is open seasonally – and only two hours a week (if that; check the website for times), people come from near and far for recitals, to see where these organs were manufactured, and, in Sept. 2024, they’ll come for the International Reed Organ Society’s EsteyFest 24! If you’re into organ music, you might want to come, as well.

Fire Arts Gallery and Studio Brattleboro VT

SHOP: Fire Arts Vermont 

Even if you can’t afford the glass or ceramic art (both made in on-site studios), be sure to stop into Fire Arts Vermont (on Rt 30) to see their striking, Instagram-worthy showroom.

Penelope Wurr Shop, Brattleboro VT

SHOP: Penelope Wurr

Though famous for her glass vases and bowls, Penelope Wurr specializes in artful things UK. Homegoods, gifts, accessories, books – she’s all about contemporary European style, with a distinctive British accent. You’ll find her shop in downtown Brattleboro.

Gallery in the Woods, Brattleboro VT

With three floors of hand-made crafts from all over (56 New England artists), you really won’t know what to ogle first at Brattleboro’s Gallery in the Woods. It’s a kaleidoscope of a shop, with lots of things you won’t find anywhere else.

PHOTO OP: Creamery Covered Bridge

I did get all exited when I first heard about this covered bridge – the last surviving 19th century covered bridge in Brattleboro. It’s not that my heart leaps whenever I see a covered bridge, although they are lovely and nostalgic. I got my hopes up because, after the Creamery Bridge was closed to vehicular traffic, I thought I’d find ice cream in there. But no. It’s Creamery only in the name, not the function. Just giving you a heads up.

Brattleboro VT Restaurants

Roofdeck, Whetstone Station, Brattleboro VT

EAT/DRINK: Whetstone Station (*Closed For Renovations)

River views, arched-steel bridge views, and brews; what could be better on a temperate eve? For now (summer ’24), Whetstone Station is under renovations. Check the website for updates.

Brattleboro VT Hotels and Rentals

STAY: Naulakha – Rudyard Kipling’s Home in Vermont

Soak in some seriously literary vibes at Naulakha, a rental home with an incredible pedigree. Famous British author of Jungle Book and other stories for children, Rudyard Kipling, lived in Vermont for several years. This house, just outside of the town of Brattleboro, was built for him in 1892.

With four bedrooms, and three baths (starting at $575/night, $3450/week, three night minimum), it’s great for a large family or group of bookworm friends. Sing “The Bear Necessities” or “I Want to Be Like You,” with your kids while romping around Kipling’s things. Much of his original furniture remains, which means that guests can sit at the very desk where the famed author wrote The Jungle Book, Captains Courageous, and portions of the Just So Stories.

Exterior, Four Columns Inn, Newfane VT

STAY: Four Columns Inn, Newfane

This iconic, whitewashed 16-room “Country Inn,” a dozen miles from Brattleboro, was shuttered in 2013 and reopened, afresh, in mid 2015, changing hands again in 2022. Once enchanting enough for the likes of Mick Jagger (who stayed over for his 40th birthday), it had fallen off its imperial pedestal and was recently purchased by Chef Andrea Jordan, who’s given it new French twist.  A Maven Favorite – the Inn has its own post HERE.

STAY: The Inn on Putney Road

No room at Four Columns? Visitors also rave about The Inn on Putney Road in Brattleboro VT.


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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1 thought on “9 Romantic Things to Do in Brattleboro VT: Be Jungle Book Adjacent”

  1. Strolling of the heifers – love it. This town looks pretty cool, thanks for the detailed article and putting it on our radar. Gotta love any place so dedicated to beer.

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