Woodstock, Vermont, just about three hours by car from Boston, is a quintessential New England getaway, especially for autumn leaf-peeping. Together with its surrounding towns of Quechee, Bridgewater, and Plymouth, this area ticks all the Vermont-core boxes: fall foliage, covered bridges, and craft beer and spirits. Grab your hiking boots and camera and prepare to sip maple-infused cocktails and sample cheddar based on a recipe from late President Calvin Coolidge’s dad.
8 a.m. breakfast at Soulfully Good Cafe
Start your day at Soulfully Good Cafe, inside a pink house with white picket fence that encloses a cute patio dotted with umbrellas — weather-permitting, it’s people-watching paradise. The thoughtfully decorated interior makes you feel right at home with its loungy couches and full bookshelves. Load up on breakfast fare such as avocado toast and omelets, or grab a fruit parfait to go.
Activity interlude: Stroll through town
From breakfast, stroll southeast along pedestrian-friendly Central Street, lined with shops selling flannel, books, gifts, and art — in particular, Collective is a lovely cooperative showing off many artists’ works. A short detour north onto Elm Street leads to more gems like Village Butcher Shop, whose sandwiches are superb fuel for later activities, and family-owned general store F.H. Gillingham & Sons, selling the likes of pickles and penny candy here since 1886. Back down Central Street, you’ll soon enter the heart of Woodstock — the town Green, ringed by historic buildings like the public library from 1883 — and spot the Middle Covered Bridge over the Ottauquechee River. This bridge is a relatively new replacement from 1969; worthy of a postcard, it stretches nearly 140 feet across the river, protected from snowy winters by a sturdy roof.
9:30 a.m. coffee at Abracadabra Coffee Co.
Before you tackle any major outdoor activities, make sure to stop by Abracadabra Coffee Co., which takes the surprising form of a vintage white Shasta camper nestled inside a barn off Route 4. The selection of single-origin coffees takes you on a journey to the coffee belt, from Peru to Costa Rica, and little snacks like Liège waffles and caneles make perfect companions.
Activity interlude: Hike the Pogue and Mt. Tom trail
About a half-mile walk north of the town center is the entrance to Marsh-Billings-Rockefeller National Historical Park, where you can hike the 4.2-mile Pogue and Mt. Tom loop that immerses you in the sights and sounds of fall. The Pogue, a scenic little pond sandwiched between the nearby mountains, is a good place to stop for a snack. If you’re up for an easier and shorter route, you can go around the Pogue via Prosper Road, which is about 2.5 miles and takes about one hour to complete. You can also combine this activity with a visit to the nearby Billings Farm and Museum, a historic working dairy farm with a sunflower labyrinth, seasonal exhibits, Jersey cows and draft horses, and cheese made on-site.
12 p.m. lunch at Mon Vert Cafe
After the hike, refuel at Mon Vert Cafe back on Central Street. Owner Samantha DiNatale purchased the cafe from previous owners in 2015 and has since expanded the chalet-style house into a 3,100-square-foot space with two floors of seating plus a patio. Be sure to order the Monte Vert Cristo, a savory challah French toast sandwich with pan-fried ham and melty Cabot cheese that comes with a side of real maple syrup. Just as importantly, the menu has an extensive vegan and vegetarian selection that ranges from breakfast burritos to mushroom sandwiches, with fresh bread from Vermont’s Red Hen Baking.
Activity interlude: Shop the Quechee Gorge Village
About a 15-minute drive east, in Quechee, you’ll find this charming collection of attractions and stores. Wax nostalgic over Pez dispensers and Star Wars lightsabers at the Toy Museum, then unearth vintage toys among the fine china and art sold by hundreds of vendors at the Vermont Antique Mall — or pick up modern ones at Vermont Toys and Games. Stock up on Vermont-made souvenirs like cheese, wine, and maple syrup at the Quechee General Store, and get the farm-to-closet experience at Vermont Alpaca Store, which sells scarves and sweaters made from the wool of the adorable rescue alpacas outside. If you get thirsty, sample gins made with wild Vermont juniper berries and vodka distilled entirely from local maple syrup at Vermont Spirits Distilling Co.
Alternative activity interlude: Hike the Quechee Gorge
If you prefer to stretch your legs some more, this is the deepest gorge in the state, affectionately dubbed “Vermont’s Little Grand Canyon.” You can appreciate it from the Quechee Gorge Bridge spanning the Ottauquechee River, or get a closer look on a short, easy hike of about 1.3 miles.
4:30 p.m. visit to Whistlepig Whiskey Parlour
Part of Quechee’s historic Parker House has been transformed into a tasting room for Whistlepig, distillers of some of the country’s finest rye whiskey. The second-floor tasting room is all inviting leather sofas and dim lighting, with antique picture frames telling the history of the house. Some rarities are available only on the premises, such as the 18-year double malt rye aged in virgin oak barrels, and a 12-year cask rye aged in a combination of oak, Madeira, sauternes, and port barrels. Note that it’s free to visit but you have to reserve a 30-minute appointment in advance.
Alternative: Beer at Long Trail Brewing Co.
A 15-minute drive west of Woodstock, grab a beer at this brewpub right on the Ottauquechee River. Though most New Englanders can pick up the long-standing brewery’s famous Long Trail Ale at their local liquor store, the taproom always offers something special, including limited-edition brews like a barrel-aged version of Triple Bag, a whopper at 11 percent ABV. While you’re out this way, don’t miss the President Calvin Coolidge Historic Site, a museum at the birthplace of the 30th president of the United States, and Plymouth Artisan Cheese, which uses the same building and cheddar recipe from 1890 that Coolidge’s father did.
5 p.m. glassblowing and dinner at Simon Pearce
U.S. presidents have been known to give Simon Pearce’s high-quality glassware to foreign dignitaries, and the company’s flagship store and restaurant in Quechee is an adventure unto itself. It occupies a historic mill overlooking a picturesque dam, Mill Pond Falls, and the Quechee Covered Bridge, and most days if you come early for a 6 p.m. dinner reservation you can watch glassblowers at work, shop the allegedly imperfect seconds, and then have a creative cocktail at the bar. The restaurant’s atmosphere is simply grand, with floor-to-ceiling windows, brick walls, and polished wooden floors. Much of its menu rotates seasonally, possibly including horseradish-crusted cod or vegetable pappardelle with wild mushrooms, though some signatures like a creamy Vermont cheddar soup remain constant.
9 p.m. cocktails at Au Comptoir
Back in Woodstock, this relatively new cocktail bar has a patio and stays open later than most competitors — although only till 10 p.m. (Sorry, night owls.) Spirits made by nearby Mad River Distillers are a mainstay on the cool yet cozy bar’s eclectic menu, from a sidecar based on apple brandy to a barrel-aged Negroni incorporating maple-cask rum. Seasonal mocktails hit the spot as well. Not a cocktail person? Interesting wine and beer offerings include an aged cava from Catalonia and the Alchemist Beer’s eternally coveted double IPA, Heady Topper.
Right downtown, the Blue Horse Inn is a local landmark that became a bed and breakfast in the 1980s, and it’s hard to beat the experience of floating in its heated outdoor pool overlooking the river. The newly renovated Woodstock Inn & Resort, another central option, offers plenty of luxury amenities like a spa, a tennis court, and an 18-hole golf course; Red Rooster restaurant and Richardson’s Tavern are on the property, too. Toward Woodstock’s western edge, the Lincoln Inn & Restaurant features its own beautiful views of the Lincoln Covered Bridge, and the restaurant’s ever-changing tasting menus draw plenty of discerning diners.