The Perfect Three-Day Weekend in Manchester, Vermont

Whether you’re looking for the perfect fall getaway or a few days on the slopes, the small but trendy town of Manchester, Vermont, has quickly become one of the best areas in the state for every season. Only a four-hour drive from Manhattan and a two-hour drive from Boston, Manchester is easily accessible for a three-day vacation while also embodying the quintessential Vermont town with white church steeples, local breweries, fantastic restaurants, dynamite art galleries, and many other attractions. Manchester transforms from a snow-covered ski town in the winter into a lively arts and hiking magnet in the summer and fall. With the addition of a Kimpton hotel, the Taconic, right in the town center, it’s even easier to hunker down and relax by the outdoor fire pit while enjoying Manchester’s idyllic scenery. There’s never an off-season for this classic Vermont town.

Day 1

If you’re arriving in the early afternoon, drop your bags off at the Taconic Hotel and head into town via one of the hotel’s bikes, or go for a leisurely stroll. Noodle around the town’s center and hit up some of the many premium outlet stores or unique mom-and-pop shops. The afternoon should end with some time spent at the famous Northshire Bookstore. Prepare to delve into a good book or simply browse through their one-of-a-kind photo books while sipping a latte at the adjoining Spiral Press Café. (Tip: if the stomach starts to rumble, try the curry chicken salad sandwich.)

Since it’s the first night, chill out and relax for the rest of the evening at the Taconic. The hotel’s restaurant, the Copper Grouse, has quickly become of the best eateries around and uses seasonal, locally sourced ingredients. For a pre-dinner hors d'oeuvre, try the Vermont cheese plate and one of the many specialty cocktails or craft beers. You can either dine by the cozy fireplace in the lounge or grab your drinks and sit outside around the fire pit. Even though the menu changes every season, the Copper Grouse burger is a classic staple.

Day 2

Quickly rub the sleep from your eyes and scurry to the popular Up for Breakfast. Keeping to its name, the small eatery is on the second floor of an old building, and those who don’t want to wait should get there on the early side (they don’t take reservations, or credit cards). This country-style breakfast-only spot is best for a hearty omelette or the restaurant’s celebrated morning glory pancakes served with hot Vermont maple syrup.

When you're feeling sufficiently satisfied, jump in the car and head to Bromley Mountain. If you’re visiting in the summer, Bromley’s slopes feature an alpine slide that runs multiple courses from the middle of the mountain. They also have one of the longest ziplines in Vermont, perfect for those who love a serious adrenaline rush. In the fall, the resort opens its lifts for leaf peepers. During winter months, snow bunnies should get there early and buy a half-day ski pass. Although the mountain is smaller than its neighbors like Stratton and Stowe, you’ll rarely wait on a lift line, and since the mountain faces south, the slopes stay a bit warmer when the temperature drops to the single digits.

Tuckered out from a morning of activities? It’s time to head back toward town and spend the afternoon at the Southern Vermont Arts Center. Before fully immersing yourself in the exhibits, sit down for a quick lunch at the Japanese-inspired Café Sora. The menu is simple but fresh, with great bites like a ginger pork sandwich or miso soup. The Arts Center is open year-round and exhibits a diverse range of work, from outdoor sculptures to photographs, abstract paintings, Cubist portraits, and classical landscapes. If the great outdoors still beckons, the property has acres of hiking trails as well as the Boswell Botany Trail.

After a full day of gallivanting, a low-key evening will feel good. For some traditional and upscale Vermont fare, drive a few minutes out of Manchester and feast at the Perfect Wife. Manchester is not known for its raucous party scene, but you can grab a nightcap and listen to some live music at the Equinox Resort’s Falcon Bar or rock back and forth on a porch chair and do some stargazing back at the Copper Grouse.

Day 3

When you’re visiting Vermont, always make a food pilgrimage to a classic, quintessential American diner for a hearty breakfast. In this case, Manchester’s Bob’s Diner is the best in the neighborhood. Forget avocado toasts and chai lattes, because Bob’s is all about traditional grub. The iconic establishment has everything from eggs over easy with buttered toast and a cup of black java to mini buttermilk flapjacks with the perfect amount of melted butter and powdered sugar. You’ll feel like you’ve walked back in time with the steel countertop molding, red cushioned barstools, and a colorful 1950s jukebox.

From the diner, drive north on Route 7 for 15 minutes to the Mountain View Ranch for some leisurely horseback riding. Vermont is known for its trail rides, and the most unique way to see some of the mountain peaks or rolling farmlands is by saddle. Depending on your skills and comfort level with a horse, choose a one- or two-hour ride, either private or with a group. You can also sign up for a Sunset Ride, Picnic Ride, or even rodeo-style lessons. In the winter months it’s a bit harder to go for a trot when the trails are covered in feet of snow, so opt for the ranch’s sleigh rides. Hop in the sleigh and snuggle up in a plaid blanket all the way to a campsite where the ranch provides some necessary cold-weather sustenance like hot chocolate.

By noon, it’ll be time to get the horses to the stable and drive back to Manchester for lunch at Depot 62. The Mediterranean restaurant sits inside a quirky antiques shop with private tables near the window and a copper communal table in the middle. The menu is all about brick-oven pizzas, lamb kebabs, and baklava—a nice change of pace from the classic Vermont dishes.

The last afternoon of your trip should be dedicated to a bit of history and culture, so it’s time to check out the famous Hildene House—former estate of President Lincoln’s son, Todd. The property is over 400 acres, which includes the formal gardens, a carriage barn, Sunbeam Pullman car, and many other enticing attractions. When it snows, the grounds turn into cross-country skiing and snowshoeing trails. One of the most notable pieces on display in the Georgian-revival mansion is President Lincoln’s stovepipe hat. Another part of the mansion not to miss is the 1903 Pullman car. This traditional train car has a sunbeam roof and was used at the turn of the century as one of President Teddy Roosevelt’s train cars during his presidential campaign.

To end the perfect three-day trip, after checking out some art galleries post-Hildene House, the final dinner should embody both the old and new Vermont––and that means the Silver Fork. After living in Puerto Rico for 20 years, the husband-and-wife team behind the Silver Fork decided to bring a little heat to the mountains. The eclectic menu features Puerto Rican–inspired dishes and seasonings, but changes daily depending on what the chef finds at the market or simply what’s making him feel inspired that day. A reservation is essential since the restaurant only has six tables and five barstools. (Tip: The Silver Fork is closed Sundays, so if your last day in Manchester is a Sunday, switch this with your Copper Grouse dinner night.)

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