Woodstock is the ideal place to escape the city for a Vermont weekend getaway, whatever the season. And there is so much to do, that our guests always wish they had stayed longer! So on your next visit, plan on staying at least 3 nights with us for a refreshing and relaxing time.

Here’s what your next Vermont getaway could look like:

Your arrival to Woodstock and the Woodstocker B&B
Arrive between 3pm and 7pm — drop your bags at the B&B and walk to town. River Street will take you alongside the Ottauquechee River, through the covered bridge, right on the Green!
Take in the scenery of this picture perfect New England town, with private houses and public buildings representative of late 18th to late 19th century architecture. Stroll down Central Street with its independent shops (more on these later), then circle back on Elm Street and head to The Prince and The Pauper for cocktails and an unforgettable dinner in one of Woodstock’s oldest and Vermont’s most famous restaurants. Reservations recommended (we’ll handle that for you).
Tip: Book our Romance in Woodstock Package, and get a $100 gift certificate to spend at The Prince and The Pauper

Day 1: Forget your car and hit the outdoors, then discover Woodstock
After a solid breakfast (think cheddar omelet and local whiskey fennel sausage, side of roasted potatoes, intro’ed by hearty country bread and homemade brioche), hike Mount Tom right outside our B&B. There is a trailhead on Faulkner Park, right behind The Woodstocker. It’s a smooth, healthy walk up most of the way, with switchbacks that make the hike easy, until you hit the last 100 yards. There, a few rock outcrops make the last stretch a little more challenging, but ropes are there to help you through it. Once atop Mount Tom, take in the breathtaking view of Woodstock (selfies are encouraged!). Then, continue on a smooth path through the most picturesque countryside towards the Pogue, a lake favored by turtles. Then choose the long easy way down towards Route 12 and Billings Farm. Once at the bottom there’s an option to visit the Rockefeller mansion, or head right onto Route 12 and stroll downtown through Elm Street.
Get some rest with lunch at Mon Vert Cafe or Soulfully Good Cafe. Both offer wonderful foods, trendy and cozy decor, and sidewalk seating.
The afternoon will fly by on Central and Elm streets, lined with independent stores such as Yankee Bookshop, Vermont’s oldest independent bookstore; Gillingham’s General Store, family-owned since its foundation in 1886 (check out their antique Otis elevator, and grab a bottle of wine to enjoy later); art venues such as the Woodstock Gallery, the Gallery on The Green, the Art Collaborative, or Fossil Glass; gifts shops Unicorn and Clover (the latter also now offers CBD products); Danforth Pewter; clothing boutiques — enter at your own risk… these shops (in no particular order) have simply amazing stuff: Phlox, 37 Central Clothiers, Sudies, Footprints, Who is Sylvia (Vintage clothes), Encore (high end consignment store), Elevation Clothing and Woodstock Sports for top notch sports clothing; and last but not least The Vermont Flannel Company, because everyone needs a flannel!
Back at the B&B, you’ll take your bottle of wine or beer out to our fire pit or the library and enjoy with the munchies we put out in the afternoon (think hummus, soppressata, or chocolate melt).
Dinner at Mangalitsa, the new and exceptional farm-to-table restaurant no one should miss when visiting Woodstock. Reservations are required, and this gem of a place fills up fast, so as soon as your room is secured with us, let’s make sure you have a dinner booked there as well! We’re happy to assist you with that.

Day 2: Hitting the farms
Billings Farm and Museum hugs Woodstock on its North side, right beyond the Ottauquechee River. More than just providing the town with a most bucolic backdrop, it is an intrinsic part of Woodstock’s identity. The farm, a working farm and museum with Jersey cows, sheep and draft horses, is deeply steeped in land conservation and environmental protection. After viewing the award-winning documentary A Place in the Land recounting the estate’s history over a century and a half, you will walk around the different buildings and the grounds, partake in the activities scheduled throughout the day, and visit the restored 1890 farmhouse. Mostly, you’ll be talking to the people who maintain this incredible place and they will open up your perspective.
Next, you’ll continue alongside the Ottauquechee River, on oh-so-Vermonty dirt roads, up on the hills north of Woodstock and unto Sugarbush Farm. There, you’ll take a walk through the sugar maple woods and learn how the sap is collected, then turned into syrup in their maple house. You’ll taste the different grades of maple syrup. You’ll discover how aging affects the taste of cheddar cheese and find out which is your favorite. You’ll buy a bunch of Vermont products made right there to take home with you. Before leaving, you’ll be sure to say hi to their – huge – Belgian work horses.
You’ll keep the evening casual and quality-driven with dinner at Worthy Kitchen. You will hop in the car for – literally – 5 minutes and cross town to this hip place featuring an amazing selection of craft beers, creative dishes and a quality approach to classic, comfort foods. There is outdoor seating and live music on certain evenings. Order at the counter and take a buzzer with you.

Day 3: Take it outside the confines of Woodstock!
East of Woodstock: Quechee
On the way to Quechee, stop at Andrew Pearce bowls a few miles down Route 4, on the left. Andrew Pearce is known for wooden bowls carved out of a single piece of wood. Tip: Shop their seconds, they are spectacular and at softer prices!
Then, stop in Quechee for:
– A hike or a segway tour down the gorge
– Shopping at Quechee Village: don’t miss Whisper Hill, our amazing provider of bathroom products made with essential oils; Vermont Spirits, a great local distillery; Cabot cheese official tasting station; the Vermont Antique Mall
– Simon Pearce Glass and Restaurant in Quechee, right at the waterfall. Watch and interact with the glass blowers until 9pm every day on the lower level. Brunch or dine at the restaurant after a tour of the beautiful shop.
– Vermont Institute of Natural Science. VINS is an environmental education, research and avian rehabilitation organization set on 47 spectacular acres. Enjoy their live raptor exhibits, feeding times, visit with their reptiles, and more. Check their daily schedules! And don’t miss a hike on their grounds.
West of Woodstock: Bridgewater and Killington
On your way out, stop at the Farmers Market less than a mile out of town for some amazing local foods to bring home, including our own provider of maple syrup, Maple Crest Farm in Woodstock and some wonderful cheeses (We love Timberdoodle from Woodcock Farm). Other stops on the way:
– Farmhouse pottery on Route 4. The shop exudes luxurious simplicity, with most products in declinations of soothing whites. We love the adjacent potters’ workshop where you are invited to step in and chat with the potters while they are working.
– Shackleton Thomas in Bridgewater: furniture and pottery at an elevated form. We love the naked table project!
– Long Trail Brewery. Visit the brewery from an elevated platform, have a bite next to the river, sample some beers (or just plain have one) and buy a pack to bring back home! We love the setting and the decor.
– Killington, aka The Beast. The largest ski resort on the East Coast has a ton of things to do in the summer: downhill mountain bike, hiking trails, ATV, Segway, the Wrecktangle, and for golfers: the golfboard!

More options:
Outdoorsy? Rent a bike in town, pack a picnic prepared by your favorite innkeepers at the Woodstocker B&B. Warm up on the bike trail through town, down by the river behind Billings Farm, then ramp it up and explore the bike trails on Mount Peg. Later this summer, take it a notch up at Elemental Bike Park, scheduled to open at the Suicide Six Ski area late July: six miles of bike trails accessible by the resort’s new quad chairlift.
In the mood for some pampering? Try First Impressions, Splendid Chaos, or the Spa at the Woodstock Inn and Resort.
There is much more to do in Woodstock, but we think that’s a pretty solid start.

mountains at sundown, big blue sky turning gold, and trees green and turning gold and red.

Woodstock, VT: your ideal getaway

The Ideal Three-Day Vermont Weekend Getaway was last modified: May 4th, 2024 by Isabelle Chicoine