Vermont

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Grafton Village Cheese Company

There’s a misconception that fall is Vermont’s only season, but one trip in the summer can change any mind. Swimmable rivers, electrically verdant hills, flash-thunderstorm-infused weather and extremely friendly folks make it enchanting.

After shooting up Route 22, a speedy alternative to the Taconic, we headed east on Route 9 into historic Bennington and then onto the mountainous Molly Stark Trail, which bridges Bennington and Brattleboro and is perhaps the only designated “scenic byway” we traveled that lives up to its name. 

The tininess and isolation of bustling Wilmington, the first real town you come to after lots of climbing, give it the feel of an alpine village. Top off the ascent with lunch and a beer on the shady back deck of the Vermont House Tavern (15 West Main St, 802-464-9360).

We made it to our first evening respite, the ultrasecluded Inn at Cranberry Farm (61 Williams River Rd, Chester; 800-854-2208. From $145 including breakfast), in time for a walk to a nearby waterfall. Our room was so cozy we picked up an excellent takeout dinner from Raspberry & Thyme (on the Green, Chester; no phone) and fired up the stove to ease the night’s chill.

Before heading north into the mountains, we took a detour to the pristine village of Grafton—a once thriving town of 10,000 that fell into disrepair after losing its industries in the early 20th century. Refurbished by a wealthy New York bank magnate in the ’60s, it now offers up the Grafton Village Cheese Company (533 Townshend Rd, 800-472-3866), where you can sample award-winning fromage.

A winding drive north on 100 brought us to the mammoth Jackson-Gore Inn (77 Okemo Ridge Rd, 877-952-2576; from $163), Okemo Mountain’s most luxe ski resort. After checking out the nearby Buttermilk Falls, a series of cascading streams and swimming holes, we kicked back for afternoon drinks and a parade of wild turkeys.

Heading north on 100 along Lake Rescue and then Echo Lake, which made us vow to come back and plant ourselves on its shores someday, we eventually alighted at Woodstock’s modest Pond Ridge Motel (506 Rte 4 West, 802-457-1667; from $79), whose biggest draw is hidden from the road: 4.5 acres of sprawling lawn that stretch down to the edge of the swimmable Ottauquechee River.

The next day, we turned all too sadly home. Maybe that’s why we took the long way—across Route 4 past Killington and down Route 7. It’s not designated at all, but the mesmerizing beauty of the road finally put the word scenic to shame.

THE TAB

Three nights, two people
Jeep Liberty
enterprise.com

Car rental $550
(with gas)

Hotels  510
+ Meals 440
TOTAL $1,500

Travel time 4hrs

Choose a getaway:

• New Hampshire: Wide empty space and cozy inns make a perfect pair.
• Cape Cod: Sand dunes and salty air await.
• The Brandywine Valley: Pork-inflected delicacies and palatial mansions are just two hours away.
• The Adirondacks: Fresh-baked pies, quiet lakes and old-school ski jumps.
• Vermont: Journey to a Green Mountain high.