Woodstock, For Jocks

June’s a month when athletes outnumber tourists in one of Vermont’s most scenic towns. 

Woodstock is one of those Vermont towns that’s so cute, you suspect it was made for tourists. And it was–sort of. The town has been a vacation destination since the turn of the century. In 1934, Mary French, a granddaughter of Frederick Billings, and Laurance Rockefeller were married in theCongregational Church. Since then, the Rockefeller family has done much to preserve the old colonial buildings, bury power lines and set up the Marsh-Billings Farm and Museum, part of the Marsh Billings Rockefeller National Park.

Woodstock still attracts people from all over the world. They stay at the sprawling Woodstock Inn, woodstock-town-crier-signwindow shop the ower- lled streets or, in the winter, try skiing at Suicide Six. But there’s another side of Woodstock: the one that draws Vermonters and athletes from around New England.

As Dan Webb, who runs Gear Traders, a sports consignment shop, notes: “There are so many things here that most people don’t think about. The Ottaquechee River, for instance, has sweet Class II rapids up near Bridgewater and some Class III right in town. There’s hiking and shing and mountain biking–the list goes on.”

In June, that list gets even longer. On June 4, the Covered Bridges Half Marathon takes runners through the regions’ prettiest routes. Registration is known to sell out as soon as it opens on the first Monday of December. But if you miss your chance, there are plenty of other excuses to visit.

Catch the Forest Exhibit at the Vermont Institute of Natural Sciences (on display through September). Sign up for the Long Trail Century Ride out of nearby Bridgewater (June 24), brave the crowds at the Quechee Balloon Festival (June 16-18) or if you’re feeling strong, ride the Class IV back road sand trails on the Overland Grand Prix (Aug. 17), a grueling 49-mile timed gravel ride/race that has attracted such cycling legends as Ned Overend.

Or, just spend a weekend here in June before the crowds descend. We’ve got your itinerary covered.


Your first stop is family-owned Woodstock Sports, where owner Peter Johnston and his mascot, a Viszla named Brody, will point you in the right direction for just about any activity under the Vermont sun, along with the gear to go with it. The bike shop features high end bike kits, Scott and Fuji bikes, along with maps of some great road rides in the area, including a 22-miler that will take you through two covered bridges.

For dinner, head to the 100-seat Worthy Kitchen where, at an outdoor table, you might start with the Worthy poutine (loaded with duck fat gravy and smoked Plymouth cheddar) and move on to the Buttermilk fried chicken or the brisket melt. You can pair the comfort meal with one of 18 local beers and three wines on tap.

Bed down at the 506 On the River Inn, where you can re-energize with the bistro’s affogato, made with vanilla-bean ice cream, a shot of espresso and chocolate covered coffee beans, before hitting the indoor pool for a few late-night laps. Then it’s time to tuck into the softest of sheets at the 40-room property, which is stylishly decorated with finds from the owners’ travels around the world. A fitness room, game lounge, hot tub and sauna, plus a huge country breakfast are included in the stay.


Get up early for a 30-minute hike to the summit of Mount Tom, a 1,250-foot peak that offers wonderful views of surrounding Woodstock. For longer excursions, both the Long Trail and the Appalachian Trail run through the area. For a hike on the AT, try the West Hartford Road to Cloudland Road section, which passes over Bunker Hill, where Revolutionary War veterans once made a stand. There are many clearings with open views, hill top pastures and old cellar holes.

Back in town, stop by the Woodstock Farmer’s Market for coffee and scones before visiting Farmhouse Pottery for a look at how artisanal potters Zoe and James Zilian have crafted some of the most sought-after bowls, bakeware and pitchers in the state.

Some of the newest mountain biking trails around town are the fun, flowing singletrack around the Woodstock Aqueduct. For longer routes, head to the Killington Mountain Bike Park, where there are 27 miles of trails and lift-served riding.

By now, you’ve earned an 80-minute sports massage at the Woodstock Inn, where spa guests get to sip tea and munch on granola by the fire in the airy lounge before being led up to treatment rooms for a combination of massage and light stretching designed to improve blood flow.

Dinner at Lincoln Inn

For dinner, treat yourself (if you feel like splurging) to a 12-course dinner at the Lincoln Inn, voted one of the 10 best new restaurants in America for 2016 by Forbes Magazine. Owner Mara Mehlman came across the inn on a bike tour, fell in love with it and moved from England with her partner, top chef Jevgenija Saromova.

Or, on a warm spring or summer evening, nothing beats dining al fresco at Richardson’s Tavern at the Woodstock Inn. Menu items include stuffed oysters on the half shell, pancetta-crusted salmon and pear tart tatin with salted caramel sauce.


Formed by glacial activity nearly 13,000 years ago, Quechee Gorge is the centerpiece of Quechee Gorge State Park. Several Route 4 viewing spots allow you to peer down to the Ottaquechee River that flows 165 feet below. The Quechee Balloon Festival, held here every June (and this year June 16-18), is a highlight. Follow up explorations of Quechee Gorge with a refreshing swim in nearby 215-acre North Hartland Lake.


Don’t miss a stop at Simon Pearce, whose eponymous owner and operator is the Irish-American glassblower and potter. After browsing through the items on display, sit down for Sunday brunch at Simon Pearce’s Mill, overlooking the town’s covered bridge and the Ottaquechee River. Afterwards, work off the calories with a paddle on the river or a trail run at Billings Farm, an 1871 dairy farm that’s part of the national park.

Don’t leave town without stopping off at Gear Traders, located on the corner of Elm and Green in the same building where Wallace Bertram (nicknamed Bunny) discussed building the first rope tow in Vermont some 90 years ago. It’s a great place to drop off lightly-used gear or pick up a used kayak, bike carrying case or anything else you might need.

After, grab an early supper or a lunch of Cobb salads and devil-on-horseback Panini at Mon Vert Café.

You earned it.

Sarah Tuff

Sarah Tuff writes about outdoor sports, health and fitness from her home in Shelburne; her work has appeared in The New York Times, Runner's World and Skiing, among other publications. She is also the co-author of 101 Best Outdoor Towns (Countryman Press).