August 2019 Vermont Vacations: How to Spend a Long Weekend in the Green Mountain State

Vermont Vacations: How to Spend a Long Weekend in the Green Mountain State

Twin Farms’ Barn Cottage.
Twin Farms’ Barn Cottage.
From epic bike rides to elevated IPAs, blueberry picking to pottery classes, summers in Vermont are sublime.

You have to love a hotel that’s built for the perfect summer bike ride. From the stone pillars at the entrance to Twin Farms in Barnard, Vermont, it’s an effortless ten miles – downhill all the way – through red-clover meadows and birch forests to the picture-book village of Woodstock. Chef Nathan Rich sends you off with a box lunch of sandwiches on homemade bread and still-warm chocolate chip cookies. The return trip is just as sweet: The resort drives you back.

Vermont vacations in summer are a breezy pleaser if you do them right. On an extended weekend, the Green Mountain State lives up to its billing, with endless possibilities in those pine-colored hills and a rare sense that getting the most from a place sometimes involves taking it easy. Cell service isn’t a guarantee in the woodsier spots, which describes much of Vermont, so it’s fine to ditch the devices and pick blueberries or perhaps some blackeyed Susans instead. And because average temperatures hover around 70 and daylight lingers past 9pm, summer tends to overdeliver in these parts.

I live in California but make a Vermont vacation an essential stopover this time of year. August doesn’t feel like August unless I spend part of it with a cheese-trail map in hand, sniffing around for an award-winning cheddar, or greeting five o’clock with a frosty IPA in a state dubbed the “Napa Valley of beer.”

“In any season, Vermont is all about being outdoors and beholding the beauty of fresh streams, crisp mountain air, and a classic American sense of freedom to roam,” says Virtuoso travel advisor David Ourisman. “And Twin Farms makes an ideal, casually luxurious base from which to take side trips into nature and one cute town after another.” Here’s how to get the most out of a Vermont vacation during a three-day stay.

Fly-fishing at Copper Pond.
Fly-fishing at Copper Pond.

Day One: Woodstock and Twin Farms

It was a modest price to pay for true love. In 1927, when Nobel Prize-winning novelist and playwright Sinclair Lewis asked journalist Dorothy Thompson to marry him, she agreed, but on one condition: that he buy her a farm with vast lawns, lavish orchards, and “delicious air” – and it had to be in Vermont. The place they found was a Revolutionary-era farmhouse (they paid $10,000 for it) on a parcel that’s now home to Twin Farms.

The lush, adults-only getaway, with just 20 rooms and cottages spread across 300 acres, last year celebrated its 25th anniversary as one of America’s most exclusive retreats. It’s only two and a half hours from Boston but might as well be “a country unto itself,” as Pearl S. Buck once described the whole of Vermont. The resort’s six private ski runs double as hiking and biking trails in summer, and there’s art inside and out by such museum-worthy painters and sculptors as Jasper Johns, David Hockney, Milton Avery, and Frank Stella. Summer is a time for kayaking or fly-fishing on Copper Pond in the morning, often followed by long, lazy naps and afternoon mint juleps on the croquet lawn.

The old Yankee magic isn’t limited to the resort. Billings Farm & Museum in Woodstock is a working dairy-cum-award-winning history project on Vermont’s rural heritage – a country store, traditional farmhouse, and farm workshop in one. It’s what everyday life here looked like a century ago. Across the road lies Marsh-Billings-Rockefeller National Historical Park, devoted to conservation history and land stewardship. Tour the historic home of pioneering conservationist George Perkins Marsh or head straight into 555 acres of forest, with more than 20 miles of maintained trails.

A culinary creation from chef Nathan Rich. 
A culinary creation from chef Nathan Rich. 
Back at Twin Farms, dinner begins with Champagne and nibbles in the main house beside a crackling fireplace (nights cool down even in summer) before chef Rich serves whatever’s fresh from the property’s herb, vegetable, and fruit gardens, and nearby farms such as Kiss the Cow and Fable. The hotel’s wine cellar stocks some 15,000 bottles, and the dining vibe is pure Vermont farm country. As Ourisman says, “You’re treated like royalty without having to put on a jacket and tie for dinner.”

Day Two: A Scenic Drive through the Green Mountains 

Practically anywhere you drive in Vermont is a scenic route (it helps that billboards are prohibited). One worthy ride heads north from Barnard past Silver Lake until Route 107 curls west into the Green Mountains. From there, Route 100, edging National Forest land all the way to Killington, is considered by many to be the prettiest drive in the state. Calvin Coolidge’s meticulously kept boyhood home is off 100A, offering a portal to a time when a small-town Vermont kid could become president. Route 4 loops you back to Woodstock past two preserved covered bridges – one in Taftsville, the other in Quechee.

Whether you get to Woodstock by car or epic bike ride, it’s essential to see the town on foot. Laurance Rockefeller, who adopted the village after marrying Mary French, granddaughter of railroad magnate and resident Frederick Billings, worked hard to preserve Woodstock’s nineteenth-century character, going so far as to bury the power lines. Fun fact: The free summer trolley is powered with electricity generated by cow manure from local farms.

Serious comfort food from Worthy Kitchen.
Serious comfort food from Worthy Kitchen.
Worthy Kitchen is an outstanding place for a craft beer, seasonal dishes, and, OK, handcut fries cooked in Wagyu beef tallow (you’re on vacation!). Woodstock Farmers’ Market, indoors and open year-round, is a supernova of local organic produce, meats, and cheeses. Open since 1935, The Yankee Bookshop is the longest-running bookstore in the state, and you’ll keep it going longer once you discover its impressive selection of Vermont authors. At Farmhouse Pottery, Zoe and James Zilian run a thriving ceramics studio with a modern homewares boutique and offer “couples clay dates” for you and your significant other to take a turn behind the potter’s wheel.
A “flying session” at New England Falconry.
A “flying session” at New England Falconry.

Day Three: Falconry Lesson, Cooking Classes, and More 

Keep an eye overhead as Chris Davis hands you his business card. It says “Master Falconer,” and it’s worth starting the day with his 45-minute intro “flying session” at New England Falconry’s historic Rutherford Barn in Woodstock, where trained Harris’s hawks will alight on your gloved arm with unspeakable majesty. At Kelly Way Gardens, job titles to ponder include butter churner, beekeeper, spirits infuser, and dairywoman. Cooking classes and culinary gatherings, held in a big red barn, celebrate the splendor of the Vermont farm table in summer. Spoiler: You’ll want to marry one of those heirloom tomatoes.

Then again, you’re excused if you just want to loll around at Twin Farms. Rooms are palatial – even the smallest is 650 square feet – and stocked with fresh coffee, beer, wine, and snacks, all complimentary. Most accommodations have views of the mountains and meadows, with soaking tubs and porches where you can hurry up and do absolutely nothing.
Handmade wooden puzzles from Stave Puzzles. 
Handmade wooden puzzles from Stave Puzzles. 
One amenity not seen elsewhere: a custom jigsaw in each room by Stave Puzzles, a family-run Vermont business since 1974. The hand-constructed wooden brainteasers are considered heirlooms and sell for many thousands of dollars. You find them everywhere around Twin Farms, including at The Pub, a hidden parlor alongside a covered bridge, where you can sip some very good whiskey, crank up the old Wurlitzer jukebox, and piece together a few mysteries before the rest of life comes calling on Monday.

At Twin Farms, Virtuoso travelers receive a welcome amenity and breakfast daily. 

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