Manchester, nestled between the Green Mountain and Taconic Mountain ranges in southwest Vermont, has long been a popular getaway for New Yorkers seeking respite from city life. A destination for second-home owners, it has a year-round population of about 4,500 that swells to as many as 12,000 people in the summer, according to John Burnham, executive director of the Manchester Business Association.
Often compared to tony Stowe or Woodstock, the town has an upscale ambience. Visitors might stay at the luxurious Equinox Golf Resort & Spa or Kimpton Taconic Hotel, with Bromley and Stratton mountain resorts for skiing nearby. The Manchester Designer Outlets feature brands such as Brooks Brothers, Vineyard Vines and Polo Ralph Lauren.
Yet the town's rich history sets it apart from Vermont's other resort destinations. Manchester Village was among the first places in New England to be developed and advertised as a summer getaway. Many U.S. presidents vacationed in Manchester, including William Howard Taft, Ulysses S. Grant, Theodore Roosevelt and Benjamin Harrison. Abraham Lincoln's son Robert took such a liking to Manchester that he bought a summer estate in town — now open to the public as a museum.
Overlooking Manchester Village stands the towering spire of the First Congregational Church, founded in 1784 and notable for welcoming Vermont's first Black pastor, in 1818. Ye Olde Tavern, opened in 1790 and Vermont's oldest inn, remains operational today as a restaurant transporting customers back to colonial times. The independent boarding school Burr and Burton Academy, established in 1829 as a seminary, later became the state's first coed secondary school.
Located on the picturesque Battenkill River, Manchester is also the birthplace of the fly-fishing store Orvis, which claims to be the oldest mail-order retailer in the U.S. Today, the Orvis fly-fishing school offers lessons to refine casting techniques, and practitioners of the sport can show off their skills at the American Museum of Fly Fishing's annual festival in August.
Further demonstrating New Yorkers' interest in Manchester, the New York Times wrote a "36 hours in Manchester, Vt." story in 2014. Visitors definitely could spend 36 hours in this vibrant resort town, but in keeping with our spin-off series' concept, we offer an itinerary for exploring like a local — three to six hours at a time.
Start the day at Up for Breakfast, a brunch spot cleverly named for its location up a flight of stairs. The menu, featuring pancakes, omelettes and huevos rancheros, has remained relatively unchanged for the past two decades, co-owner Wojtek Wierzbicki said. A local favorite is the hearty Hungry Hiker: two eggs, two pancakes, two sausage links, two bacon strips, toast, coffee and home fries. It's best to arrive early to avoid lines. People tend to comment on "how small it is and how busy it is," Wierzbicki said. "But, you know, it kind of gives it that homey vibe."
For a quicker bite, head to Willoughby's Depot Eatery, famous in town for its freshly baked doughnuts. Indulge in bestsellers such as the honey dip or maple cream, or try something new with the maple bacon or PB&J flavors. Named after owner Courtney Callo's late dog, Willoughby, the eatery also offers an array of sandwiches, each of which is "connected to a dog and their personality," Callo said. The signature Willoughby sandwich? Egg, sausage and cheddar cheese sandwiched between doughnuts and drizzled with maple syrup.
Next, browse the stacks at Northshire Bookstore, a locally owned establishment spanning 15,000 square feet, with more than 60,000 books in its inventory. A collection of 500 rare books includes Harry Potter and the Goblet of Fire signed by J.K. Rowling for $4,000, The Supreme Court: How It Was, How It Is signed by late chief justice William Rehnquist for $1,000, and a first edition of the 1936 Margaret Mitchell novel Gone With the Wind for $400. Afterward, unwind with a beach read and a latte at the Colburn Café, conveniently located inside the bookstore.
You may also want to pick up a history book as inspiration for the next stop, Hildene, the Lincoln Family Home. Explore the Georgian Revival mansion where Robert Todd Lincoln and his wife, Mary, resided in the summer; stroll the gardens; and step aboard a restored 1903 wooden Pullman car that will transport you back in time.
Grab lunch at Al Ducci's Italian Pantry, an Italian grocery store and deli featuring fresh cheese, imported meats, and homemade dishes such as eggplant parmesan and lasagna. Co-owner Patricia Vunk said the store makes her nostalgic for her childhood in an Italian neighborhood on Long Island.
A crowd favorite is the three-meat sandwich, packed with salami, soppressata, capicola, roasted peppers, fresh mozzarella and basil, drizzled with oil and vinegar. And, as Vunk put it, customers "go crazy" for a pasta dish — penne with creamy marinara and housemade sausage — that is only made on Saturdays. "People will wait hours for it to be ready," she said.
Alternatively, head to Moonwink, which has been the only Burmese restaurant in the state since Essex Junction's Irrawaddy closed in 2023. Co-owner May Stannard, who cooks her native Burmese cuisine, is currently running the restaurant as a one-woman show while her husband, Wes, recovers from septic shock. Help this beloved local gem stay afloat while enjoying traditional Burmese dishes such as Oh No Kou Swel, a creamy coconut chicken noodle soup with a hard-boiled egg, cilantro and lime.
Take your food to go for a picnic on the summit of Mount Equinox, accessible by car via Mount Equinox Skyline Drive. Owned by the Carthusian monastic order, the path is the longest privately owned paved toll road in the U.S. Drive carefully as you navigate hairpin turns and climb 3,248 feet to summit the tallest mountain in the Taconic Range. At the top, enjoy panoramic views and amenities including picnic tables, restrooms and a meditation room. On the way down, be sure to give your car's brakes a rest at the designated pull-off points. Even my sturdy Toyota RAV4 started sputtering during the steep descent.
Back in town, compete with your friends for the highest scores at Pastime Pinball, where $27 buys unlimited play on more than 60 vintage pinball machines. Co-owner Beth Friedman describes the arcade as a "playable pinball museum." Bounce through pinball history on machines set up in chronological order of release date, starting with a Humpty Dumpty-themed game from 1947. Upstairs, a snack bar offers craft beer, nachos and ice cream sundaes.
Pastime Pinball is not your average Dave & Buster's. "We didn't want an arcade vibe," Friedman said. "It's a more upscale version: bright, airy and very, very clean."
People looking to learn about pursuits even more niche than pinball should consider visiting the American Museum of Fly Fishing. "You kind of have to know the sport to get anything out of this," gallery assistant Bob Goodfellow admitted.
Despite not being an angler myself, I enjoyed exploring the world's largest collection of fly-fishing-related artwork; learning about the legendary "king and queen of fly-fishing," Joan and Lee Wulff; and marveling at King Charles III's fishing vest.
If you're eager to experience fly-fishing firsthand, visit the Orvis flagship store next door, where customers can practice casting and feed fish at the pond out back. The store also hosts a free Fly Fishing 101 course on Sunday mornings, a cost-effective alternative to the $279 lesson at Orvis' fly-fishing school. "People come from all over the globe just to say they've caught a fish in the Battenkill," general manager David Carlsen said.
Conclude the afternoon at the Southern Vermont Arts Center, a sprawling 100-acre campus with numerous art exhibits, a sculpture garden, a café and a 400-seat theater. The venue doubles as a museum and a shopping destination, with much of the featured artwork available for purchase. Past exhibits have ranged from "For the Love of Vermont: The Lyman Orton Collection" to "The Red Dress," a garment that's been to 51 countries and is continually embroidered as it travels the world.
For dinner, Depot 62, offers a one-of-a-kind experience: a Turkish restaurant inside a furniture store. Munch on warm pide — a traditional puffy bread topped with sesame and black cumin — surrounded by colorful sofas, stacks of ornate rugs and funky chandeliers. Try the Konya kebab, lamb meat slow-cooked in a wood-fired oven and served in a traditional earthenware pot called a güveç.
Save room for after-dinner drinks and small plates inside the Crooked Ram or in its outdoor space, the Yard, open from May to October. Known for exceptional cocktails, fine spirits, and a curated selection of natural wines and craft beers, the Crooked Ram was recognized as one of Esquire's 27 "Best Bars in America" in 2021. Pair a drink with the top-selling Bianca Roni, a Neapolitan-style white pizza with pepperoni that's become so popular the restaurant now features it on a T-shirt.
Finish the day with music at Earth Sky Time Community Farm, a three-generation family farmstead with a bakery, inn and concert venue. Among the upcoming artists are Lakou Mizik, a collective of Haitian musicians formed in the wake of the country's devastating 2010 earthquake (August 4); and Saints and Liars, a Vermont-based Americana band (September 8). Like Manchester itself, the venue still feels like small-town Vermont — with a pinch of influence from different corners of the world.