Where to Thrift, Wander, and Eat Local: A Day in Southern Vermont

Aug 18

If you’re the kind of traveler who’d rather find a vintage linen blouse than hit a big box store—or who considers a really good farm stand haul the highlight of a trip—you’ll feel right at home in southern Vermont.

This region is full of quiet charm and creative spirit: Vermont vintage shopping, riverside trails, independent bookstores, and local food that actually tastes like something to write home about. Whether you're staying at Tanglebloom Cabin or just passing through, here’s how to spend a slow, satisfying day exploring Brattleboro—a small town with a big heart.

Brattleboro Vermont day trip from Tanglebloom — *photo Ethan Abitz*

Morning: Coffee, Markets & Meandering

Start your morning slow—because that’s how southern Vermont moves best. If you’re staying at Tanglebloom, enjoy your first cup of coffee or tea on the front porch, with birdsong for company, before heading out.

Then, ease into the day with a stop at:

☕ Fire Arts Café
Located in a former firehouse next to an art gallery, this café serves up excellent espresso drinks, fresh pastries, and a warm local vibe. A perfect start to your Brattleboro day trip.

🍓 Brattleboro Farmers' Market (Saturdays, seasonal)
This market is beloved for good reason: music, shade trees, and a joyful mix of local food, handmade goods, and global street food (don’t miss the dumplings or the tamales). Ideal for stocking up on picnic fare or finding a meaningful gift.

📚 Everyone’s Books
This fiercely independent bookstore is a must-visit for readers of all kinds. The shelves are packed with fiction, poetry, environmental writing, cookbooks, and radical reads you won’t find everywhere else.

Midday: Vintage Hunting, Small-Batch Treats & Local Eats

After a morning of wandering, it’s time to treasure hunt—and treat yourself.

🪞 Twice Upon a Time
A charming vintage shop offering everything from antique dishware and handmade baskets to mid-century glassware and cozy wool layers. It’s the kind of place where you’ll lose track of time—and leave with a story.

🍫 Tavernier Chocolates
Equal parts boutique and art studio, Tavernier crafts small-batch chocolates inspired by local ingredients and landscapes. Expect foraged flavors, beautifully designed packaging, and truly delicious souvenirs (if they make it home).

🥙 Yalla
Just down the street, Yalla is a bright, casual spot serving flavorful, Mediterranean-inspired food with Vermont ingredients. The falafel is crispy, the hummus creamy, and the specials board often surprises in the best way.

Afternoon: Scenic Wandering & Farm Stand Hauls

Once you’ve eaten and thrifted your way through downtown, wind down the day with something slower. Southern Vermont offers unstructured beauty in every direction.

🚗 Grassy Brook Road Loop
A beloved route for cyclists and scenic drivers alike, this rural road takes you past open fields, old barns, and forest-framed vistas. It’s a gentle, soul-soothing way to explore the countryside, just steps (literally!) from the farm.

🌊 West River Trail or Local Swimming Holes
Take a short riverside walk on the West River Trail, or bring a towel and head to the West River or Rock River swimming holes for a refreshing dip. Both are less than 15 minutes from the cabin.

🍅 Roadside Farm Stands
Keep an eye out for tucked-away farm stands—many operate on the honor system and offer seasonal treasures like fresh herbs, heirloom tomatoes, local eggs, and wildflower bouquets. Some of our favorites include Wild Carrot Farm, Rebop Farm, and SUSU CommUNITY Farm.

Evening: Back to the Cabin

By now, your tote bag may be full of books, vintage finds, and the makings of a Vermont picnic.

Head back to Tanglebloom Cabin and:

Cook a simple dinner with your farmers’ market haul
Sip something cold on the porch as the light shifts across the hills, and sparkles on the river below
Watch fireflies spark to life, one by one
Soak in the wood-fired hot tub under the stars

This is what Vermont does best: unhurried days, sensory pleasures, and deep rest.