As fall foliage encompasses the Northeastern United States both overhead and underfoot, many travelers, myself included, find our trips can often include seeing these beautiful vibrant colors. When a family wedding took my boyfriend and I out of our Los Angeles apartment to Western Massachusetts, we decided to get an extra day of fresh, chilly air and drive just an hour to Brattleboro, Vermont. While we didn’t feel the need to stay overnight, this town makes for a perfect day trip or stop as you are passing through to other Vermont destinations.
Duchess Coffee
Of course, if you have read my previous blogs at this point I’m sure you can tell I’m both a coffee connoisseur and a lover of aesthetically pleasing design. Light and airy with pink accents and live plants, Brattleboro’s Duchess Coffee is a third wave coffee shop doubling as a bookstore that serves up rich libations in an Instagramable location. They source their beans from woman owned farms in South and Central America. These are then roasted onsite in Vermont (you’ll get a peak at this while you wait for your coffee). Each cup is made with attentive precision and care. There is a comfortable couch inside, as well as a small amount of outdoor seating.
Retreat Farm
The lands of Retreat Farm are open to the public every day from dusk till dawn. Believing that land is not owned by anyone but available for free access for all, the stewards of Retreat Farm maintain alluring hiking trails and gardens for the community. Of course, our favorite part was seeing the animals in their pastures. While the farm is home to only half a dozen animals, it’s worth a visit to see Carlos the ox and his companion goat Pip. If traveling with children, check out their “storybook walk” which allows kids to read a short book as they walk from station to station in the forest. This leads you to The Fiddlehead, a living sculpture that provides views of the farm and river beyond. Initially established to provide food and outdoor therapy for Brattleboro Retreat patients, this farm is a staple of the town.
Retreat Tower and Cemetery
To add a bit of spooky October vibes, we headed into the woods. The Retreat Tower from 1887 was built by patients of the Vermont Asylum (later known as the Brattleboro Retreat) in the hopes that the patients (suffering with mental health issues) would be aided by the fresh air. Sadly, it is thought that a few of the patients took their lives from the tower, leading many to believe the grounds haunted. Just a short distance from the tower is the Brattleboro Retreat Cemetery (also known as Asylum cemetery). This cemetery was used to bury patients between 1842 and 1901. As you respectfully walk around these woods, watch your head as the land doubles as a disk golf course. While the haunted nature of this hike made it perfect for the Halloween season, the trails are beautiful and worth visiting anytime of year. Parking can be found on Cedar Street in the lot for the Harris Hill Ski Jump.
Madame Sherri House
Cross the Connecticut River, which acts as a border between the states, to briefly enter New Hampshire. While you cannot climb the stairs, you can walk on top of what remains of the Madame Sherri House, a once vibrant 1930’s home. Placards at the beginning of the short walk to the ruins (which is the start to more extensive hikes) describe this French entertainer’s extraordinary life, culminating in her throwing extravagant parties at her beloved estate before it burned down in 1962. Now, the surrounding land is named Madame Sherri Forest and hiking trails lead guests through the beautiful natural landscape, featuring bridges going over small ponds and wildlife scampering through the brush.
The Works Cafe
While there are several good lunch options within the center of town, we settled on The Works Cafe. As my boyfriend has celiac disease (meaning he is allergic to gluten) we were excited that they were able to make him a panini that avoided cross contamination. I opted for the comfort of warm, gooey, mac and cheese complimented by a chai latte. We’ll admit, the day we visited seemed to be a stressful one for the staff, but the delicious food and cozy wood accents made up for this.
Downtown Brattleboro
Brattleboro’s downtown is steeped in character, with art deco brick facades and a variety of eating and shopping options. Stroll through the streets to admire the architecture of the local churches. If spending the night in town, plan to see a show at Stone Church, a unique live music venue. Or spend your time popping into equally unique shops, such as Beadniks or Everyone’s Books. Unfortunately, River Garden Market Place, a beer hall/restaurant/craft market/entertainment venue, was closed the day we were visiting (they are closed Tuesdays and Wednesdays) but a quick peek through the windows ensured that this is a must do if you are visiting a different day of the week.
Brattleboro Museum and Art Center
In 1972, locals wanting to save Union Station, a historic train station, from demolition opened the Brattleboro Museum & Art Center. With no set admission price, visitors can pay what they wish (they recommend $5-$10). Note that the museum is closed Mondays and Tuesdays. You’ll need approximately one hour to fully explore the various exhibits. When we visited, there was an excellent showcase of art created with felt that even included an interactive piece. We were also fans of the Nebizun: Water is Life series. Their exhibits change regularly but no matter what is on, it is sure to intrigue.
Whetstone Beer Co.
As fond as I am of starting my day with coffee, I’m as equally as fond of ending it with a beer. As previously mentioned, my boyfriend (and quite often my travel partner) has celiac disease. While using the Find Me Gluten Free app, we discovered Whetstone Beer Co. We snacked on chips and fries as I sampled the house’s Rug Life (a delicious Amber Ale) and my boyfriend downed a can from Groundbreaker Brewing (a gluten free brewery out of Portland, OR). The atmosphere was rustic meets industrial, much like the town, and would be the perfect place to cap off a day with friends. Located right across from the art museum and where the Whetstone Brook feeds into the Connecticut River, their two vast outdoor decks offer amazing views of the river and forest beyond.
Creamery Covered Bridge
On our way out of town, we had to hit one of the fall bucket list items Vermont is known for – a covered bridge. The Creamery Covered Bridge is closed to cars but open to foot traffic and makes for excellent autumnal photos. Relax while walking through this 1879 piece of local history as you listen to the babbling Whetstone Brook below. If visiting on a Saturday between May and October, you can be treated to the Brattleboro Area Farmers Market just next door from 9am-2pm.
Other Top Posts!
Your Ultimate Trip To Kauai: Exploring the East Shore
From the logistics of hotels and rental cars to the fun stuff like beaches, rum tastings, and lighthouses, we’ve got you covered on Kauai’s East Shore!
Top 7 Things to do in Seward, Alaska: Your Epic 48-Hour Itinerary
From a glacier hike and boat tour of Kenai Fjords National Park, to coffee on the water and fish chowder downtown, we’ve got you covered on planning your next trip to Seward, Alaska!
Ultimate Scotland 8 Day Travel Itinerary (Part 3)
Through the Cairngorms to Edinburgh, let the third and final part of this Scotland 8 day travel itinerary help you start planning your next adventure today!
Ultimate Scotland 8 Day Travel Itinerary (Part 2)
From the Isle of Skye to Loch Ness and Inverness, let part 2 of this post help you plan the most epic Scotland 8 day travel itinerary!
Ultimate Scotland 8 Day Travel Itinerary (Part 1)
From Edinburgh Airport to Glencoe and the Isle of Skye, let part 1 of this post be your guide to an ultimate Scotland 8 day travel itinerary!
Perfect 3-Day Itinerary for Prague, Czech Republic
From the city’s red roofs to the walls of the “Yellow Submarine” pub, there is plenty of history to explore in Prague; medieval and modern.