Story by Maria Buteux Reade
To reach Woodstock, follow Route 4’s meandering curves along the Ottauquechee River, a relaxing approach that mirrors the town’s unhurried spirit. Beautifully maintained Georgian brick homes with picket or wrought-iron fences and stately trees line the streets. Woodstock is geared for strolling—once you score a parking spot and remember to keep the meter well fed. Immerse yourself in the plethora of independent shops, art spaces, booksellers, and eateries. Well-heeled Woodstockers take genuine pride in sharing their polished community with visitors in all seasons.
3pm Time to stretch your legs and get some exercise! Head to the Woodstock Inn & Resort’s Nordic Adventure Center just outside the village and explore Mount Tom and Mount Peg. Rent cross-country skis, skate skis, or snowshoes and hit the 30 km of well-groomed trails.
6pm Now that you’ve worked up an appetite, drive three miles farther south to the Kedron Valley Inn in South Woodstock. Grab a seat at The Ransom Tavern’s bar and sip a frothed Lambro Sour, a refreshing and light pink cocktail with Lambrusco syrup, bourbon, and lemon, then wander into the dining room and watch your Neopolitan-style pizza emerge from the imported Italian oven. Try the “Old Orchard,” made with local apples, cheddar, lardons, and arugula, or another favorite—broccoli rabe with fennel sausage. Hearty salads celebrate produce grown at the inn’s gardens.
Simran Johnston, 29, born and raised in South Woodstock, moved back home from Brooklyn to breathe new life into the 1828 inn, which has 24 rooms spread among three buildings. The Johnston family also owns the adjacent South Woodstock Country Store where you can stock up on all your Vermont essentials. All this a mere 7-minute drive from the Woodstock village green!
9am Rustle out of your warm nest and slide into a wooden booth at Mountain Creamery on Central Street. For 30 years, this home-style family diner has perfected from-scratch country breakfasts. Order a fluffy loaded omelette or glug some pure maple syrup over a stack of buttermilk pancakes or a pile of French toast. Many of the meats and veggies come from the owner’s Hinterland Farm in Killington.
Slopesters can spend the morning at Suicide Six, the oldest ski resort in the nation (established in 1936). This family-friendly resort’s varied terrain welcomes beginners and challenges experts. The cozy lodge is perfect for an après ski sip and snack. Looking for a non-ski option? Get a taste of Vermont agriculture at Billings Farm & Museum, a fully operational dairy farm with a
beautiful herd of tawny Jerseys. Explore the livestock barns and wander through the interactive farm-life exhibitions to gain a better sense of Vermont’s dairying history. Open weekends in January and February; closed in March.Then check out Sugarbush Farm where you can sample their 15 flavors of waxed cheddars and the four grades of maple syrup produced on the third-generation family farm.
1pm Need an energy boost? The wizards at Abracadabra Coffee offer all manner of high-octane beverages and adventurous signature drinks from single-origin beans roasted on site at this funky hidden gem. Warm up with a nitro draft horchata: espresso, oat milk, mole bitters, vanilla, cinnamon, and maple syrup. Nibble a freshly baked hand pie, decadent pastry, or see what the food truck parked outside dishes up. Peruse tie-dyed merchandise and other curated retail goods while listening to the unique collection of vinyl spinning all day long. Weekends only, 9am–2pm.
If you crave a fresh pint and serious farm-based comfort food, Worthy Kitchen has you covered. Try the Kitchen Burger (two smashed burgers), Worthy Mac (cavatappi with roasted garlic cream, Plymouth cheddar and parmesan, and crumbled croissant topping) or the Chixwich (a buttermilk-fried succulent chicken thigh sandwich). Take a deep dive into Vermont’s renowned craft beers and ciders.
3pm Revived, now it’s time to stroll and shop.
Start at F.H. Gillingham & Sons’ General Store, a revered institution since 1886. This delightfully sprawling shop carries everything from vintage candies to Carhartt clothing, cast iron to camouflage, kitchen utensils to ukuleles. Lose yourself in old-time fun!
Elevation Clothing offers stylish gear for active living. Here’s where you can find all things Patagonia, Barbour, Skida, Ice Breaker’s lightweight New Zealand merino wool base layers, and an entire wall of colorful Darn Tough socks.
Jeffrey Kahn opened Unicorn, an eclectic shop of curiosities, in 1978. Browse the quirky gifts—from hippie (hand-blown smoking paraphernalia) to high tech (vacuum-sealed water bottle complete with Bluetooth speaker for your outdoor adventures). Check out the collection of unusual pocket knives (from $20 to $1,000). Unicorn is the place to look for anything and everything from a Roman glass inlaid pendant to Woodstock wind chimes. And yes, there is an entire section devoted to unicorns.
Fossil Glass is a cozy shop and art studio filled with sand-blasted etched glassware, carved polished stone, elegantly sculpted vessels modeled on tree-like forms, and low-fire pottery bowls with interiors finished in luminescent 22K gold. Cristina Salusti received a Fulbright scholarship and has done artistic residencies at the MacDowell Colony and in Japan. She creates truly world-class art worthy of a museum, but equally suitable for a fortunate home.
Prepare for an authentic time warp when you descend into Who Is Sylvia? Poke through the high-quality women’s and men’s clothes and accessories from the Victorian era through mid 20th century. Rated a Top 5 Vintage Shop in New England, this shop has been passed down from woman to woman for 40 years.
Collective – The Art of Craft (a striking granite edifice and former linseed oil factory in the 1820s) is home to a juried cooperative of 13 artisans. One of five Vermont State Craft Center Galleries, the Collective is filled with ceramics, woodenware, forged metals, jewelry, fiber arts, sculpture, and paintings. Meet the makers themselves who help staff this inspiring gallery.
Still want more art? Woodstock has several notable galleries including Gallery on the Green and The Woodstock Gallery, both at the center of town.
Bibliophiles can lose themselves in Pleasant Street Books (a sanctuary for rare and antique volumes) or shop for the latest titles at The Yankee Bookshop.
Valentine’s Day is almost here and if you’re looking for an exquisite piece of jewelry for a special someone, Ferro Jewelers specializes in both regal estate pieces and custom jewelry. Their merchandise is to die for and the staff couldn’t be more accommodating or hospitable.
6pm Start the evening off with a craft cocktail or glass of wine at the Red Rooster lounge within the Woodstock Inn. Then wander up Central Street to the rustic and intimate Mangalitsa. Co-owners Matt Lombardo and Chef Nick Laurendeau worked together at the luxe Twin Farms in Barnard before opening this venture in 2017. Nick honors the seasonal produce grown specifically for him a few miles away at Fat Sheep Farm in Hartland. Tall Mason jars of Nick’s house-preserved and canned sauces, pickles, and veggies fill a glass case in the entry and serve as the basis for his earthy creations. While contemplating the concise farmhouse menu, sip a hemp flower–infused negroni with CBD honey or slide into “The Comfort Zone” (Monkey Shoulder whiskey, fresh mint, lime, ginger liqueur, and maple syrup). Entrees highlight handmade pasta, local braised meats, and shellfish, including a rotating selection of crudo. Treat yourself to the duck confit or duck breast with parsnip, pear, and black garlic accompanied by a side of crispy Brussels sprouts with a dollop of whipped feta and eggplant relish. Sample small plates such as lobster and butternut twin ravioli with squid ink and Thai basil, or grilled oyster mushroom with persimmon, Bayley Hazen blue cheese, and sesame honeycomb granola.
One floor below, The Daily Catch serves Sicilian-style seafood dishes. Paul and Maria Freddura and their seven (!) sons have operated renowned shellfish restaurants in Massachusetts for 45 years. Their Woodstock location opened in September 2018. Dishes feature garlic-simmered and pan-seared seafood dishes, spicy tomato sauces, and pastas.
8am Feel like working-off last night’s meal? Swim a few laps, hit the exercise machines, or enjoy some Pilates at The Woodstock Athletic Club. Part of Woodstock Inn & Resort, visitors can purchase a day pass for $25.
10am Ease into your Sunday and soak up the relaxed vibe of Mon Vert Café. Dishes are veggie-forward. Enjoy avocado toast or a black bean and quinoa burrito with sesame ginger coleslaw. For those in need of meat, don’t miss the coffee-marinated local beef brisket with pickled red onions, basil aioli, cheese, and arugula on a baguette. Rich hot coffee and reggae will frame your mood.
Or find a seat in the cheery Soulfully Good Café across the street. Try the Farmstand herb biscuit with two eggs, roasted tomato, and Taylor ham. Order a latte and revel in a maple pecan muffin, buttery glazed croissant, cinnamon bun, or chocolate chip scone. Chef Vicki Ferentinos owned a catering business in Manhattan for 16 years and her wife, Shannon Parker-Ferentinos, is a photographer who doubles as the fastest barista in Woodstock.
12pm There’s still time to explore! So hop in the car and drive to Farmhouse Pottery. Watch through the studio window as the talented craftspeople make functional wheel-thrown stoneware. Better yet, take a wheel workshop (offered daily at 9am and 4pm). Browse shelves of hand-woven table linens, flatware, and locally made fragrant soy candles.
Drive two minutes west to the Woodstock Farmers’ Market, which, contrary to its name, is actually a high-end grocery market, not a “farmers’ market.” Check out the vast array of Vermont cheeses, charcuterie, and breads, not to mention the deli case loaded with takeaway goodies for the trip home. Choose one of the 40 sandwich options or feast on buttery cookies and muffins still warm from the oven.
Looking for one last adventure? Head east toward Quechee and visit the Vermont Institute of Natural Science (VINS) Nature Center. Weekend programs and the feeding of animals starts at 11am, and nature-based exhibitions are open year-round. Or try your hand (and feet!) at Green Mountain Rock Climbing. Take a belay lesson and tackle central Vermont’s tallest indoor climbing experience. A $20 day pass includes gear to scale the 30- to 40-foot walls with ropes and lines perfect for beginners.
Be sure to pop across the street to Andrew Pearce Bowls and run your fingers across the satin-smooth, hand-turned wooden bowls, boards, and plates from locally sourced black walnut and cherry. Bring home a piece of Vermont as an enduring memory of your Woodstock getaway.