There is probably no more striking fall foliage in America than the bright colors and deep blue skies of autumn in Vermont.

And the most charming destination in Vermont might well be the village of Woodstock. The media agrees. Woodstock was described by Ladies Home Journal and Yankee magazines as “the Prettiest Small Town in America.” The Boston Globe called it “almost ridiculously pretty.”


Travel & Leisure magazine added, “In Vermont they call it “leaf peeping,” a phrase one-part awkward and one-part charming—as if the people doing the looking were catching nature in flagrante. Technically they aren’t wrong: “in flagrante” translates from Latin to “in blazing,” and what are these stately Vermont mountains, undulating Vermont forests, in autumn if not ablaze with color? Periods of peak foliage, when the leaves are at their most riotous and vibrant, move from the north of the state to the south, and from its highest elevations to its lowest, as fall progresses. Gorgeous vistas lit up with gold, orange, yellow and red (and everything in between) are visible from mid-September through mid-October, but it’s a good rule of thumb to head farther north the earlier it is.”

Check the foliage color by date here.

One reason Woodstock is such an idyllic village is that in 1934, Laurance Rockefeller adopted Woodstock as his summer home, and as the years passed the Rockefeller family’s contributions to the Vermont town grew considerably. The beautiful village owes much of its charm to the family who helped preserve its historic and rural feel by building the Woodstock Inn, a center point for the town, and paying to bury the village’s power lines underground. Their commitment and devotion to the town’s architectural heritage has been instilled in generations of Woodstock residents. Many gracious 18th- and 19th-century buildings line the streets, and much of the village is listed in the National Registry of Historic Places.

The Rockefeller family home, now part of the Marsh-Billings-Rockefeller National Historical Park, is perched atop the highest hill in the town center. The park includes Billings Farm and Museum, a working dairy farm that is one of the oldest in the country and offers visitors tours of early Vermont farm life.


Woodstock, Vermont, is 280 miles north of New York City and 150 miles from Boston. The area is served by Amtrak trains to nearby White River Junction and air service to Lebanon, New Hampshire, airport.


The large Woodstock Inn is in the center of the village and offers golf, tennis, a fitness center, and skiing.

Twin Farms in Barnard was once Sinclair Lewis’s summer retreat and now is one America’s most exclusive inns.

On the River Inn was listed in Conde Nast Travelers best new hotels of 2015

Jackson House Inn is just outside the bustling village center on three acres of landscaped gardens.

The Kedron Valley Inn is several miles south of the village, near the Green Mountain Horse Association, with its miles of trails and foliage rides. The famous Budweiser Clydesdales Christmas TV commercial was filmed here.

Village Inn guests can walk to the village green, numerous art galleries, boutique shops, cafes, and restaurants. Included is a three-course breakfast served at private tables in the dining room or on the terrace in the summer months.


In town, favorites are The Prince & the Pauper and Melza Bistro, locally sourced Caribbean cuisine, and more causal are Bentley’s Restaurant, with a vibrant bar scene, and The Worthy Kitchen, a local favorite.

A short drive away in Pomfret, Cloudland Farm, an on-farm restaurant to experience true farm-to-table dining. Chef Ira White creates tantalizing cuisine using fresh, local ingredients from Cloudland and other local farms—a feast for both eyes and palette. Dinner is served on Thursdays, Fridays, and Saturdays by reservation only.


Try some local craft beers. Vermont’s local beers are known far and wide. In fact, the state was recently rated as having the most craft breweries per capita in the nation. Two of the best known near Woodstock are Long Trail Brewery and Harpoon Brewery. They both offer lunch, tours, and beer tasting.

Play golf. The Woodstock area is one of northern New England’s premier golf destinations. Woodstock Country Club’s 18-hole Robert Trent Jones course is scenic and compact, but be careful—it crosses water 11 times. Quechee Country Club offers 27 outstanding holes and has hosted the New England Amateur in recent years.

Shop Woodstock. The picturesque main street is lined with boutiques, antique shops, galleries, and cafes. Two of special interest are the amazing general store, F.H. Gillingham & Sons, and the vintage fashion boutique, Who Is Sylvia?

Learn about early Vermont farm life. Explore Billings Farm, one of the finest operating dairy farms in America and a museum of Vermont’s rural past. You’ll see Jersey cows, sheep, horses, oxen, and other livestock, plus milking and butter making. Across the street from the farm, the Marsh-Billings-Rockefeller National Historical Park offers tours of the mansion and grounds.

Say cheese. Similar to the Napa Wine Trail, the Vermont Cheese Trail will lead you to cow-, sheep-, and goat-cheese tastings at almost all local craft cheese-makers.  Jasper Hill Farm cheeses captivated judges at the 2016 World Championship Cheese Contest in Madison, WI. and won two “Best in Class” awards for “Winnimere,” a washed rind, seasonal cheese and “Moses Sleeper,” a brie style, bloomy rind cheese.

Glass blowing. Simon Pearce’s glassblowing studio and shop in Quechee is hydro-powered by the dramatic waterfall outside.