Weekend Away: Woodstock, VT, Weekend Getaway Ideas

How does a romantic New England getaway sound? How about a couple’s adventure to a town that National Geographic describes as one of the most beautiful small towns in America? Couples looking to get away for a few days will find few towns prettier or more quintessentially Vermont than Woodstock, VT.

Weekend Getaway Idea: Walking downtown Woodstock, VT

White picket fences flank a verdant village green, sitting at the edge of a quaint yet lively downtown. Covered bridges connect Woodstock to acres of surrounding farmland, orchards, and hiking trails, while terrific local restaurants and breweries call visitors back to town. The historic New England character of Woodstock, teamed with the natural beauty of its forests and sophisticated elegance of its attractions, make this the perfect Vermont town for a romantic getaway. Below are just a few weekend getaway ideas in Woodstock, Vermont, for couples.

Day One — Fine Dining and a Stroll Downtown

Choosing the Woodstock Inn & Resort as a homebase for a Vermont weekend getaway is a great place to start — a stroll around the town center means simply walking out the front door. Arrive in the afternoon and do some window shopping in Woodstock, VT, before really kicking things off with a fine dining experience, Vermont style.

Romantic Inn for Weekend Getaways: Woodstock Inn, VT

Osteria Pane e Salute located in the center of town, serves up classic cuisine from northern Italy. Dishes include insalata caprese and pizza toscana, prepared with the freshest of local Vermont meat and produce. This ristorante is bumping, so make sure to call ahead and make a reservation! Those looking for a classic American bistro will love Prince and Pauper; if a Friday spent eating burgers and listening to live music sounds more your style, the Skunk Hollow Tavern oozes a Vermont ambience. Cap the evening with a walk around downtown Woodstock, or simply find a hillside with a view  Green Mountains sunset.

Day 2 — Country Breakfasts and Cultural Feasts

Head straight to Mountain Creamery for a Vermont country breakfast, complete with buttermilk pancakes and locally smoked bacon. A hearty farm-to-table breakfast, and a thick slice of local culture to boot, will prepare you for an active Vermont day. Spend your morning exploring Woodstock’s signature cultural attractions: Billings Farm and Museum and the Marsh-Billings-Rockefeller National Historic Park. Billings Farm is both an operating dairy farm and a museum that gives visitors a peek into the history of conservation and agriculture in eastern Vermont. If your kids somehow got mixed in with your luggage on this romantic getaway, they’ll love the petting zoo!

Weekend Getaway Idea: Gardens at the Marsh-Billings-Rockefeller National Park

The Marsh-Billings-Rockefeller National Historic Park (the only National Park in Vermont) is a tribute to, and evidence of, Vermont’s robust culture of conservation and stewardship, and its 20-plus miles of trails leads visitors past sugar maples, wandering stone walls and over covered bridges. Cheese hounds and syrup sippers should drive a few miles north to Sugarbush Farm, an idyllic setup with an extensive selection of Vermont’s most famous local delicacies. There, you can sample over 14 varieties of wax cheeses and all kinds of artisanal foods made with Vermont maple syrup.

If Vermont’s foodie side leaves you craving a tasty lunch, White Cottage Snack Bar should hit the spot. This Woodstock institution offers up quick, inexpensive burgers, sandwiches, and seafood, not to mention an impressive ice cream selection. Seating includes picnic tables along the Ottauquechee River out back. After lunch, go apple or berry picking (depending on the season) at Woodstock Orchards or take a hike up Mount Tom. This easy 1.5 mile hike leaves right from the center of town and the summit affords terrific views of Woodstock and the surrounding countryside.

Head back to your Vermont inn or bed and breakfast for a late afternoon rest, before gearing up for an evening at a local brewpub. Long Trail Brewing Company has made quite a name for themselves in the craft beer world, and their brewpub offers guided tours, tastings, and delicious pub fare on a shady porch along the river. Stay until you’ve tried everything on tap and then retire to the nearby 506 On the River Inn, or head back into town for a nightcap at Richardson’s Tavern or Bentley’s. Those in the mood for some entertainment can catch a movie or a show at the Pentangle Theatre right off the town green.

Day Three — Gorges and Glassware

Sometimes an early morning is one of the best ideas, even on a romantic weekend getaway. Get an early start with a morning drive to the nearby town of Queechee, Vermont. Known for its stunning namesake gorge, Queechee is a great stop for the nature lover and the connoisseur of the finer things alike. Head down to the Queechee Gorge for breathtaking views and a refreshing dip, then stop in at Simon Pearce for a tutorial in world-class glassblowing. Recognized the world over for their glassware, the folks at Simon Pearce make and sell their goods on site — a great idea for a souvenir from a memorable couple’s getaway (hint, hint, gentlemen). Simon Pearce also has a renowned restaurant, a perfect stop for a delightful brunch with a view of the Ottauquechee River before heading home.

Weekend Getaway Idea: Brunch over the river at Simon Pearce, Quechee, VT

These ideas for a weekend getaway in Woodstock really only scratch the surface of all there is to see and do in Vermont, as the Green Mountains and lush pastures are a canvas for a couple’s adventure. Paint your own landscape together, then head on back to reality with a lower heart-rate and a newfound appreciation for small-town Vermont life.

Kedron Valley Inn, South Woodstock, for couples' weekend getaways

Where to Stay in Woodstock, VT

In addition to 506 On the River Inn and Woodstock Inn & Resort, consider The Jackson House Inn, a consistent favorite for couples seeking an intimate escape. Chosen by Yankee Magazine’s editors as New England’s Best Intimate Retreat, our own panel of experts also chose this Woodstock inn as the Best Place to Kiss in New England. Other options include the Braeside Motel, set on a quiet hillside just outside of town, and the stately Kedron Valley Inn, in historic South Woodstock, which maintains a historic grandeur with a modern feel.

Photos: Woodstock Inn & Resort (first and second); Marsh-Billings Rockefeller National Park; Simon Pearce; Kidron Valley Inn.