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Middle Covered Bridge Snowy

From The Blog The perfect weekend in Woodstock: Winter edition

The gift that keeps on giving

Amid the crush of holiday shopping and planning, there’s nothing more invigorating (or deserved!) than a wintertime escape.

Two-and-a-half hours from Boston and four from NYC, Woodstock is an accessible oasis where the best of winter sports, farm-to-table-fare, local brews, and cozy, charming locales come togetherjust be sure to plan your quarantine (either in Vermont or your home-state depending on mode of travel, click here for details) and pack your most fabulously festive masks!

Get ready. We’ve got a three-day itinerary overflowing with adventure for everyone from the ski bum to the fireside sofa stalwart…

Snowy road


NOTE: Please confer with your hosts about safety precautions and guest certificates of compliance

Village living: The snow-dusted sidewalks of Woodstock’s quaint village—lined with the mullioned windows and vibrant overhangs of sundry mom-and-pop shops— will beckon just outside your door when you book a room at…

Woodstocker - Woodstock
Get cozy at the Woodstocker
Woodstock Inn snowy
Katie Berdan
The Woodstock Inn & Resort
Village Inn room 3
A room at the Village Inn

In the country: If you crave peace, where all you can hear is the sound of snow falling, or just want to get away from the hustle and bustle of it all, choose from the following accommodations:

  • 506 on the River: Riverside inn with farmhouse chic style to spare, located just outside town (plus an indoor pool available by reservation)
  • The Apple Hill Inn: Homey accommodations with hilltop views of Woodstock and Taftsville
  • Braeside Lodging: Less than a mile from the village, these rooms offer charm and convenience
  • Deer Brook Inn: Hospitality, style, and decadent breakfasts—they've got it in spades
  • Farmhouse Inn: Spend your stay on a Vermont farm with river views and a quintessential red barn that's the perfect backdrop
  • Jackson House Inn: Envelop yourself in New England charm as you sit by a roaring fire, relax in your expertly decorated room, or dine in style
  • Kedron Valley Inn: Classic, cozy, and even pet friendly! There's no better way to stay in stunning South Woodstock
  • The Lincoln Inn: Come for the food (this B&B is also home to one of Woodstock's best restaurants), stay for the Ottauquechee views!
  • Sleep Woodstock: A classic 1960s roadside motel that's affordable and right outside town (and dog-friendly, too!)
  • Woodbridge Inn: Your destination for a quaint riverside experience
  • And vacation rentals
Pool edited
The pool at 506 on the River

Day 1

You’ve made it. Breathe in that fresh air seasoned with pine and woodsmoke, then mask up and stretch your limbs with a stroll through a village scene straight from a snow globe.

Snowmen on the green facing town
Katie Berdan

Woodstock’s center—hugged from all sides by the curve of the Ottauquechee River, the gentle peaks of Mount Peg and Mount Tom, and charming Georgian, Federal, and Greek Revival homes—is a getaway guaranteed to revive.

Between admiring historic architecture and popping into family-owned establishments like Yankee Bookshop, maintain social distancing as you grab a quick bite at Soulfully Good (for their award-winning buttermilk chicken salad) and The Village Butcher (hot cider is a perfect add-on).

Mt Tom in Winter

After that invigorating outing, it’s time to freshen up at your lodging, bundle up, and head to dinner! Looking for prix fixe perfection in the country? The Lincoln Inn and Cloudland Farm are two excellent options for a culinary feast you won’t forget. Want to stay within the village? Stake your claim on an oversized lounge chair and get cozy in front of the fire as you dine at Richardson’s Tavern or visit The Prince and the Pauper for a mouthwatering meal in the charming, socially-spaced dining area. But be sure to call ahead at all the venues listed above, as reservations are required!

Richardson’s Tavern at the Woodstock inn & Resort
Jim Westphalen
Richardson’s Tavern


When the snow begins to sparkle in the morning sun, it’s time to rise and dine! Breakfast at Mountain Creamery is just the ticket—with organic eggs and local, farm-raised meats gracing the menu, you can’t go wrong. Got a sweet tooth? Grab a slice of mile high apple pie for the road. In a rush? The Woodstock Farmers’ Market and Mac's Market are perfect for quick-and-tasty breakfast sandwiches to enjoy in the car.

Now you’re prepped for an action-packed day in the great outdoors, with your choice of activities that suit you best:

Snowboarding in Vermont
Chip Allen
Ice Skating

Phew. After that doozy of a morning, are you still searching for a mid-day meal spot?

The Spa at the Woodstock Inn & Resort
Jim Westphalen
The Spa at the Woodstock Inn & Resort

If you’re heading back toward town from Killington, Ramunto’s Brick Oven Pizza in Bridgewater is serving up New York pies to-go, and we have to admit, they're hard to resist!

With a full belly, now’s the time to check in at your home base, then hit the spa for a bit of R&R for your sore après-ski muscles. A Himalayan Salt Stone Massage at the Spa at the Woodstock Inn & Resort as the snow swirls outside is just what the doctor ordered.

If you’re visiting around the holidays…

Next, head to the main entrance of the inn for a jolt of childhood magic, because a life-sized gingerbread house awaits in the lobby! Mask up and snap photos in front of this fragrant backdrop... while the ingredients are good enough to eat – resist!

Then, dinner is served! Order takeout from Angkor Wat for fresh, vegetarian-friendly Asian Fusion or make reservations to dine at The Daily Catch for seafood straight from the docks of Boston, Melaza Bistro for can’t-miss Caribbean tapas, or Ransom Tavern (featuring private room dining!) in South Woodstock’s Kedron Valley Inn for delectable Neapolitan-style pizza.

kedron valley inn
Kedron Valley Inn and Ransom Tavern

Finally, its back to your accommodations you go, to revel in snug indoor amenities like an on-site pool (506 on the River) and game room (Woodstock Inn & Resort) till its time to get some shut eye.


Last but not least: It’s your final day in Woodstock. If you awake to a whirling dervish of snow, fill your morning with snowflakes that stay on your nose and eyelashes, plus a few of our other favorite things: Mon Vert Cafe has got your order for takeout breakfast – whether you’re craving challah french toast, lox and schmear, or just a cup of joe to go.

If you’ve got little ones in tow, there’s no question, Billings Farm & Museum is your next destination (click here for safety policies)!

Billings Farm in Winter
“Woodstock” by “pushypenguin” Licensed under a Creative Commons Attribution 2.0 Generic (CC-BY2.0). Accessed 5 November 2018.
Winter snow at Billings Farm & Museum
horse-drawn sleigh ride at Billings Farm
Billings Farm staff photo
Sleigh rides around the farm.

Open Saturdays and Sundays (and some special holiday and vacation dates) during the frosty season, you’ll find a range of barnyard happenings like:

  • Visits with the Jersey herd, draft horses, oxen, chickens, and sheep tucked into their stalls
  • Take-home crafts
  • Snowshoe treks around the farm fields (bring a pair of your own or rent one from the Nordic Center)
  • Special activities during Thanksgiving at the Farm, Christmas at the Farm (complete with ornament-making and a decorated 1890s farmhouse), Winter Weekends, and even Maple Celebrations in February

As the noon bells toll, it’s time for lunch! Chow down in the farm-diner comfort of Worthy Kitchen (reservations coming November 2020) for a casual meal or the Woodstock Inn’s Red Rooster (reservations recommended) for understated elegance – and a hearty stew to warm you from the inside out.

Cue the sad Charlie Brown walk, it’s time to depart. Take a deep breath of the cold, clean air, then load up the car and glance out the window as you drive past the twinkling lights and boughs of garland bedecking Woodstock’s village shops.

Central St Christmas Decor
Katie Berdan

If you’re taking i89 or i90 and want one last adventure as the day's still young, visit the Vermont Institute of Natural Science (click here for their COVID policies) in Quechee for live raptor programs, exhibits, a glimpse into avian rehabilitation, nature trails, and a forest canopy walk offering a bittersweet goodbye: a panoramic view of this stunning winter landscape.

Special Weekend Dates to look forward to: