5 Best Things to Do in Woodstock, Vermont

Woodstock, Vermont, is one of those destinations that seem to pop up on every kind of New England “best of” list, from winter towns to foliage towns to places to see historic homes and town greens. And no wonder: Chartered in 1761, this Green Mountains town has only grown more lovely with age. Its postcard-perfect downtown is filled with preserved antique homes and buildings — Georgian, Federal, Greek Revivals — with no utility lines to spoil the timeless view. There are even three historic covered bridges still standing, including one that’s just steps from the jewel of a town green.

You could easily spend a week or more exploring this inviting and highly walkable town on the banks of the Ottauquechee River. But if you have just a day or two, here are the five best things to do in Woodstock, Vermont.

5 Best Things to Do in Woodstock, Vermont

Woodstock Inn & Resort

This centrally located historic landmark is no mere place to stay — it’s a bona fide Woodstock experience. The inn itself is deeply tied to the town’s history, having evolved from the c. 1793 Richardson’s Tavern to the c. 1892 Woodstock Inn and its later revival by Laurance Rockefeller. Beyond the lures of the inn itself — 142 distinctively furnished rooms and suites, 10,000-square-foot spa, farm-to-table dining — the property connects guests with all kinds of things to do. There’s a golf course, a Nordic center with more than 45 km of groomed trails, an activity center with mountain bike rentals, and special activities ranging from fly fishing to falconry.

F.H. Gillingham & Sons

At one of Vermont’s oldest and certainly most celebrated shops of its kind, you’ll find, oh, just about everything, most of it Vermont-centric, from postcards and maple products to clothing and local cheeses. In true New England fashion, Gillingham’s is still family-owned and now run by the founder’s great-grandsons, Frank and Jireh Billings. A stop at Gillingham’s is also sure to whet your appetite for browsing the many other shops downtown, from the Yankee Bookshop, a fixture since 1935, to Sudie’s, which specializes in modern-preppy-meets-Vermont-chic clothing.

Billings Farm & Museum

What was rural Vermont like in the 19th century? Find out at Frederick Billings’s model farm, established by the railroad magnate when he returned to his native Woodstock in 1871. Now owned and operated by the Woodstock Foundation, a non-profit educational institution founded by founded by Laurance and Mary Rockefeller, the bucolic 200-acre-plus property combines a fully operating Jersey dairy farm with educational exhibits and interactive programs and events. Visit the 1890 farm manager’s home and creamery; learn about farm work of yesteryear and today; get up close with pigs, chickens, goats, sheep, horses, and other barnyard favorites; and climb aboard for horse-drawn wagon and sleigh rides. Open seasonally.

Marsh-Billings-Rockefeller National Historical Park

At Vermont’s only national park — and the only national park in the U.S. that’s devoted to conservation history — you’re invited to immerse yourself in nature’s beauty not only via the walking trails crisscrossing the 550-acre property but also in the formal plantings around the 1805 mansion that speak to four generations of stewardship. When the mansion is open to visitors, don’t miss a chance to peek inside the stately residence, which was a Rockefeller family home until 1992. The first floor of the brick Victorian Queen Anne is filled with exquisite architectural details such as Tiffany stained-glass windows and parquet wood floors, as well as a notable art collection. Visitors’ center open seasonally.

Jenne Farm & Sleepy Hollow Farm

These two properties are among the most photographed farms in Vermont, if not all of New England, and are definitely worth stopping to see (though please keep your distance and be respectful of the fact they are private residences). Roughly 12 miles south of Woodstock, in Reading, is Jenne Farm, which has appeared on magazine covers, in photography books and TV ads, and in movies such as Forest Gump and Funny Farm. And about 3 miles north of Woodstock, on Cloudland Road in Pomfret, lies the equally picturesque Sleepy Hollow Farm, which has become a particular favorite for fall-foliage shutterbugs in recent years.

Have your own list of the very best things to do in Woodstock, Vermont? Leave your picks in the comments below!

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