Whoopie pies probably won't save humankind. But a stop at DonnaSue Bakes + Cooks in Vermont's Champlain Islands is sure to boost your faith in humanity. As soon as my mom and I see the large handwritten letters spelling out “PIE” on a sun-faded shed off Route 2 in the town of Grand Isle, we hit the brakes on our bikes. A sign next to a Betsy Ross flag informs us that Sunday business hours are “by chance.”
It's our lucky day. The door is ajar, revealing shelves of not just whoopie pies but also maple cookies, chocolate pumpkin bread, and other made-from-scratch baked goods. Inside, a freezer is stocked with sweet and savory pies. A birdhouse filled with dollar bills for making change serves as the cash register; owner DonnaSue Shaw runs her four-year-old bakeshop on the honor system.
In 2019, Shaw's four children encouraged her to start selling her addictive baked goods at the local farmers market. Just before the pandemic hit, the 56-year-old native Champlain Islander decided to try opening her own shop. Despite the unpredictability of sales over the past few years, she's kept it running, motivated by notes from customers who laud her baking prowess and sense of trust.
Thankfully, my mom and I had the foresight to rent bikes with baskets. We've already detoured to Hackett's Orchard and Allenholm Farm, both family-run apple orchards in the town of South Hero. Now we pile Shaw's signature Spicy Mikes—cream-cheese-filled ginger-cookie sandwiches—atop our bags of apples and cider doughnuts.
It's a crisp September morning in the Champlain Islands region of Vermont. We'd planned to cycle straight from South Hero to Burlington along the pancake-flat 14-mile Island Line Trail. But everything in Vermont, it seems, conspires to slow you down.
The Green Mountain State has long been a beacon for certain kinds of people drawn to the low-key lifestyle, bucolic landscapes, and progressive values. These include the many idealistic entrepreneurs my mom and I have encountered during a decade's worth of annual trips, from experimental brewers working out of garages to a chef who serves dinner-party-style meals in a general store. COVID-19 was the catalyst for the most recent wavelet of entrepreneurial energy, as natives and transplants alike saw fresh potential in Vermont's small towns, often reimagining businesses inherited from an older generation ready to relinquish the reins.
My mom and I had embarked on a road trip that started in the islands of the north, crossed the state's mountainous middle, and stretched to the pastoral southern border. We could have driven all of it in four hours, but we decided to take it slow, spending five days discovering this latest group of starry-eyed folks who, like Shaw, are running businesses on trust, passion, and a sense of stewardship.
The foliage has just started to show its famed autumnal hues, and although much of the state is already mobbed with leaf peepers, the communities along the shores of Lake Champlain are unexpectedly quiet. Sometimes called the sixth Great Lake, this massive body of water stretches for 124 miles between the Adirondacks in New York and the Green Mountains in Vermont, and beyond into Quebec. Within it is an archipelago of around 80 islands, with Isle La Motte, North Hero, Grand Isle (home to the towns of Grand Isle and South Hero), and the Alburgh Peninsula comprising what residents call “the Islands.” In the summer, their collective population of around 7,000 doubles as vacationers come to paddle, sail, fish, and camp along the shores of the area's many state parks. After Labor Day, tourists disperse, missing out on the colors and calm of the lake in fall.
The day we arrive, my mom and I pop into Hero's Welcome. First opened in 1899, this general store on the island of North Hero has been a one-stop shop for everything from groceries to local gossip. Its current owners, Vermont native Kevin White, 35, and his partner, Nathaniel Keefe, 31, took over three years ago with a mission to carry on its legacy. They've acquired a liquor license and gussied up the deli menu but have largely kept the other offerings—a book loft, ice cream, gas, and bike and kayak rentals—the same. At checkout, I comment on the surprising emptiness of the lake. “One day it will change,” Keefe says wistfully. “But for now enjoy that you can paddle into the middle of the lake during fall and feel almost like you discovered it.”
My mom and I do just that the next morning, launching paddleboards from the beach of our hotel, the North Hero House. Opened in 1891, it predates even Hero's Welcome. Guests once arrived by steamship and paid $10 a week for an all-inclusive stay. When Vermont natives Heidi Tappan and Doug Nedde heard that the 26-room hotel was destined for condo development, they purchased it. Tappan has strong ties to North Hero; her family was among the island's first settlers, her parents met as teenagers at a beach picnic, and her childhood summers revolved around the lake. Vintage family photos from the 1800s through the 1960s now decorate the inn, which Tappan has updated with bold Persian blue paint and floral House of Hackney wallpaper. A neon sign stating “We love it here” glows in the inn's new wraparound bar.
My mom and I spend the next two days falling in love with lake life. One afternoon, Captain Holly Poulin of Driftwood Tours takes us island-hopping. We spend another day reading, going for cold swims, and napping on repeat, before sipping sunset cocktails at Drifter's Boathouse Restaurant, at the North Hero Marina.
In any other state, Interstate 89, Vermont's main highway, would be considered incredibly scenic, but we leave it to head south toward Woodstock along the even more scenic Route 100, arguably New England's most picturesque stretch of road. It's particularly beautiful right now, with aspens and birches turning golden against the red maples and bronze beeches.
If Route 100 is the region's quintessential drive, then the shire of Woodstock is its archetypal town, with the requisite covered bridges, general store, village green, and a public chalkboard that acts as a modern-day town crier with news of craft fairs and birthday wishes. My mom and I have developed a certain intimacy with the place over the course of our many visits, so we quickly lapse into a routine: maple scones at Mon Vert Cafe, hiking along the trails of Marsh-Billings-Rockefeller National Historical Park, browsing our favorite shops on Central Street.
I'm delighted to see that our go-to hotel, the 200-year-old Woodstock Inn & Resort, has brightened its rooms with hits of butter yellow and cornflower blue as well as botanical-print sofas. Because of the inn's prime address overlooking the Village Green, its cozy lobby, anchored by a colossal fireplace, acts as a communal living room where guests read or sip cocoa. Au Comptoir, a short walk away, plays a similar role in Woodstock. Set within a former auto shop that once belonged to Laurance S. Rockefeller, this jewel box of a bar instantly transports us to Europe. A mix of regulars and hikers fresh off the trails settles into the 1930s Parisian café chairs to sip cocktails out of Luigi Bormioli Italian glassware. Owner Zoe Zilian hops from table to table delivering snacks like caviar served with crème fraîche and potato chips. When she sold her share of the cult Woodstock ceramics studio Farmhouse Pottery in 2020, she wanted to create a place for locals to gather and enjoy a good stiff drink. “It was hard to find a place to go out on a Monday or after 8 p.m.,” she tells us. Usually my mom and I are in bed by nine, but Zilian's smoked old fashioned persuades us to break curfew.
We're hit with more changes the next day when we visit the quaint hamlet of South Woodstock, just five miles south on Route 161. The Neapolitan pizzas at Ransom Tavern in the Kedron Valley Inn are so sensational, they've won over even the most curmudgeonly townsfolk. When owner Simran Johnston left her art career in New York in 2017 to move back to the roughly 500-person town where she grew up, she found a community that was stagnating. Her father, a real estate developer, had purchased a few struggling businesses, including the Kedron Valley Inn and South Woodstock Country Store. Johnston, 33, and her husband have transformed them in the hope of reenergizing the hamlet and attracting a younger crowd.
The general store has served the community for nearly 200 years. Once an essential part of rural life, it not only supplied daily essentials but also served as a social hub. “Amazon has facilitated convenience but also loneliness,” Johnston tells me. To lure back regulars, she's done away with clichéd souvenirs and restocked shelves with locally made or grown goods done up in pretty packaging. The café area now has Wi-Fi (and breakfast burritos), and she regularly hosts community events such as seed swaps and snow-sculpture building on the lawn.
As we continue south to the Deerfield Valley, the drive, mostly along Route 100, provides plenty of distractions beyond the colorful canopies. We stop at Mount Ascutney State Park and hike part of the waterfall-dotted Weathersfield Trail, then browse the antiques shops in Londonderry. After the state's sparsely settled northern reaches, its small southern towns feel downright cosmopolitan.
But the cocktails mixed with house-made bitters and pizzas topped with ale-infused cheddar we find here are still rooted in Vermont's distinctive artisanal DNA. Craftsmanship and community have always been valued above flashy brands and see-and-be-seen crowds. So it's not entirely surprising that when a New York–based developer tried to “Aspen-ize” the Deerfield Valley nearly a decade ago by building the Hermitage Club, a private ski resort on Haystack Mountain centered around the historic Hermitage Inn, the project went bankrupt. “No one with a private jet is flying to southern Vermont to ski,” says John Verrochi, a pandemic transplant and the co-owner of the three-year-old Deerfield Bar and Bottle Shop. “People love it here because they're nostalgic for simpler times. They're not here to show off their Bogner jackets.”
The club's bankruptcy was a defeat for the local economy but a victory for the local way of life. When it went to auction, former club members—mostly locals and Northeasterners who want to get on the slopes—organized to take ownership of the ski resort itself. When Vermont transplants Mary Lou Ricci and Tim Hall, who had recently sold their insurance company, heard that the Hermitage Inn was also for sale, they decided to purchase it. The couple consider themselves to be stewards rather than just innkeepers, positioning the property and its programming to appeal to locals as well as out-of-staters.
Fresh off a multimillion-dollar renovation, the 14-room inn packs all the magic of the Green Mountain State into its 112 acres. You arrive via a covered bridge to find a trout pond, a babbling brook, apple orchards, and a network of trails at your doorstep. The casual tavern serves a decadent truffle, mushroom, and cheddar burger, while elevated six-course menus paired with wines like Château Pétrus are served in the wine cellar as special ticketed dinners. When my mom and I rave over the crispy chicken breast roulade with earthy hen of the woods mushrooms, our server praises the chef before making sure to note that it's the area's farmers who provide the exceptional ingredients that make the dishes possible.
My mom and I found ourselves thinking about those farmers this past summer as we anxiously followed the news of Vermont's catastrophic floods. In a state built around community, we knew neighbors would rally to help one another. But we also wanted to support the business owners who have always made us feel like part of their community on our visits. By the time you read this, we will have returned. This time we plan on forgoing the bikes and driving to DonnaSue Shaw's, so we'll have plenty of room to bring a few of her homemade pies back with us.
The Champlain Islands
Where to stay
A major renovation of North Hero House reimagined rooms with thoughtful design touches and introduced a lakefront bar. The new owners of low-frills waterfront spot Shore Acres Inn & Restaurant just added a bar serving lobster rolls.
Where to eat & drink
Craft brewery Kraemer & Kin's new taproom overlooks the bay at Alburg Golf Links club. Jimmy Buffett vibes and lake views pair nicely at Drifter's Boathouse Restaurant, with lobster rolls and fries.
Where to explore
Driftwood Tours offers boat trips and sunset sails around Lake Champlain with a dose of island history. In the fall, pick any of Hackett's Orchard's 47 different varieties of apples.
The Green Mountains
Where to stay
Grande dame Woodstock Inn & Resort refreshed guest rooms and a stunning Scandi-inspired spa. Kedron Valley Inn is an updated Federalist-style inn with 17 rooms and a killer pizza restaurant.
Where to eat & drink
Au Comptoir has meticulously mixed cocktails and elevated snacks in a beautiful wood-and-brick space. Serving small-batch ice cream and maple creemees, head to Woodstock Scoops for Vermont's take on soft serve.
Where to explore
Hike Marsh-Billings-Rockefeller National Historical Park for 20-plus miles of trails lined with sugar maples and centuries-old hemlock trees. Learn about farmwork of yesteryear, wander the gardens, and sample local cheese at Billings Farm & Museum.
Southern Vermont
Where to stay
The Hermitage Inn is newly remodeled with a destination restaurant and an award-winning wine cellar. And 32-acre retreat Farm Road Estate, offers cottages and rooms in a restored farmhouse, a swimming pond, and miles of trails.
Where to eat & drink
Sip bourbon and rye at Village Garage Distillery, while noshing on chicken and waffles. Folly is a sweet family-run bistro elevating farm-fresh ingredients. Five friends transformed the Old Red Mill Inn into Valley Craft Ales, a brewery and pizzeria.
Where to explore
Kayak calm waters at Somerset Reservoir, surrounded by national forestland. Head to The Valley Trail for a nine-mile path that connects Dover and Wilmington.
This article appeared in the November 2023 issue of Condé Nast Traveler. Subscribe to the magazine here.
