where to stay
Village Lodging
If you’d like your pumpkin spice latte right outside your door, then a stay within the village is for you. Every kind of accommodation, from the grand Woodstock Inn & Resort to the river views of The Shire is at your fingertips.
B&Bs such as the Woodstocker, the Vesper, and the Village Inn offer convenience and history all wrapped into a charming package. But don’t delay – fall foliage is one of the busiest seasons in Woodstock and rooms fill up fast!
In the Country
If immersing yourself in the vibrant shades of nature is your aim, there are plenty of options for staying just outside of town:
- 506 on the River: Family-owned boutique inn on the banks of the Ottauquechee with its own bistro
- Jackson House Inn: Yankee Magazine’s choice for best couples’ retreat
- Kedron Valley Inn: Historic lodging in the heart of bucolic South Woodstock
- Sleep Woodstock: Convenient, comfortable lodging for a great price
- And vacation rentals
Day 1
BREAKFAST
Start your day in Woodstock by fueling up with a quick breakfast to go at one of our favorite local spots, Village Butcher. You can’t go wrong with a hot coffee, breakfast sandwich, or yummy baked goods.
MORNING EXPLORING
Take your breakfast to go, and enjoy a stroll around the picturesque village.
Insider tip: If you're eager to extend your trek, you're in luck! There's a river walk in Woodstock, and it begins right inside the village.
Be sure to hit Central and Elm Streets for great shops, from Woody's Mercantile, Vermont Eclectic Co, and The Woodstock Gallery, Focus - A Vermont Gallery, to beloved mainstays like the Vermont Flannel Co (‘tis the season for cozy fleece-wear) and of course the Collective, an artist owned and cooperatively run gallery.
Warm up for a moment or twenty at Clover Gift Shop, an apothecary and home-goods extravaganza, and get lost in the whimsical wonderland of Unicorn Gift Shop, while N.T. Ferro Jewelers beckons to those seeking something that sparkles.
Rainy weather options: Take the kids to the Woodstock Athletic Club pool (part of the Woodstock Inn & Resort amenities). If you are staying at the Inn you can enjoy the pool free of charge or buy a day pass. If you’re kid-free and looking for something more tranquil, The Woodstock Inn Spa is the perfect place to enjoy a massage, facial, pedicure, and all the amenities including a whirlpool, eucalyptus steam room, and sauna.
LUNCH
For something in the village grab a bite to eat at Soulfully Good Café for a delicious salad, soup, or sandwich. Another village lunch option is the Village Butcher or Mountain Creamery just a short drive outside town.
AFTERNOON ADVENTURES
If you’re joining us in September or October, head up Elm Street by foot or by car to spend some quality time at Billings Farm & Museum (great for the kids too) and Marsh-Billings-Rockefeller National Historical Park. Both locations offer breathtaking views of the changing leaves for those avid leaf peepers among us – and if you’d like a bird’s-eye view of the village, head to the top of Mt Tom via a moderate 4.2-mile round-trip loop passing rolling hillsides and the Pogue, a stunning 14-acre mountain pond.
DINNER
Eat inside or out on the patio at your choice of the historic Prince & the Pauper restaurant or Sante. You can also up the cozy factor by dining fireside at Richardson’s Tavern in the Woodstock Inn!
Craving a meal in the countryside? Get the farm-to-table experience at Cloudland Farm just outside of town– or take in the views of Kelly Way Gardens while sampling its bounty of fresh, delicious produce as part of the Red Barn Dinner Series! Reservations required.
Day 2
BREAKFAST
The leaves are falling – there’s no time to waste! Rise and shine with a delicious breakfast at Mon Vert Café or the classic diner experience, Mountain Creamery (now in its new location).
MORNING EXPLORING
Find the activity that’s just your speed: whether it’s mountain biking at Saskadena Six, the Aqueduct Trails, or Mt Peg, or taking a family tour to the treetops via the Forest Canopy Walk at VINS, perfect for up-close-and-personal leaf-peeping.
LUNCH
For a fancy take on lunchtime, enjoy a fresh, farm to table experience at Simon Pearce, overlooking the Ottaqueechee River. If you’re looking for something quick, try sandwiches and ready made items at the Village Butcher or Soulfully Good Cafe. The Woodstock Farmer's Market also has a nice selection of sandwiches, soups and salads. Don't forget a maple creemee at Scoops, located right in the village.
AFTERNOON EXPLORING
Head to Sugarbush Farm with its stunning vistas, adorable farm animals, a sugar house open for self-tours, and delicious cheeses and maple syrup made directly on the premises. Plus, the scenic drive there makes this one a no-brainer.
If you're in the mood for small bites and a cocktail or mocktail, check out Woodstock's Au Comptoir for a European feel right in the heart of the village.
DINNER
For a kid-friendly farm-to-table spot, check out Worthy Kitchen. If you're in the mood for some different flavors, check out Angkor Wat or Melaza Bistro. Craving Neapolitan-style pizza in the countryside? Do not miss out on The Ransom Tavern.
Day 3
MORNING EXPLORING
From South Woodstock head toward pick-your-own paradise. September through mid-October, apple picking is your go-to at Moore’s Orchard (at the intersection of Pomfret Road and Johnson Road in Pomfret) and Whitman Brook Orchard on Wheelock Road in Taftsville – with over 100 (yes, you read that right) varieties of apples to pick from.
When pumpkin picking season takes over, you can find gourds, squash, and your Jack-O-lanterns to-be on select dates at Fox Crossing/Ridgeline Farms on Webster Hill Road in Pomfret. Follow the country road for a taste of October in Vermont: Ox cart rides, hot and cold cider, baked goodies, and of course, fields filled with porch-perfect pumpkins!
