Reader’s Digest recently named Woodbury “the most charming small town in Connecticut.” There are plenty of contenders for the title, but we wouldn’t pose a strenuous argument. Woodbury, a leafy, historic enclave settled in the late 1600s, is set in the lush foothills of Litchfield County, and filled with 19th-, 18th- and 17th-century homes.
It’s a quiet, quaint town, with three greens, a community bandstand, and a Main Street lined with shops, restaurants, and locally owned businesses, including several fine antique dealers. It’s often called the “antiques capital of Connecticut,” and lauded as one of the best places for antiquing in New England.
It’s also home to the Glebe House Museum and Gertrude Jekyll Garden. The historic home, built in 1740, is filled with period furniture, including furniture made in Woodbury during the 18th century. The garden is being restored to the original plans created by Gertrude Jekyll, considered one of the greatest horticultural designers of the 20th century.
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Fall is especially scenic in Woodbury, where you can also explore the trails surrounding the Pomperaug, Weekeepeemee, and Nonnewaug rivers, and the more than 3,000 acres of parks, preserves, and farmland surrounding the town.
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We stayed at the 1754 House Inn, Restaurant & Tavern, located in a historic building built before 1736. It opened as an inn in 1754. Rooms are super clean with comfy beds, small baths, and simple furnishings. The walls lean and the floors are crooked and creaky, which is all part of its old-fashioned, old house charm. The best part? The inn is now owned and operated by chef Michael Bates-Walsh, who has turned the inn’s first floor restaurant and tavern into a Woodbury go-to hot spot. We enjoyed hanging out in the tavern, talking with the locals, and munching on the house-made pretzel bites (prepared in duck fat!) And we had a fine meal one evening in the main restaurant, dining on rich bowls of fire-roasted heirloom tomato soup, herb-y potato crusted cod, and well-seasoned shrimp scampi.
There are several other dining choices in this small town, including the longstanding and well-loved Good News Restaurant & Bar. The always bustling restaurant has a strong farm-to-table ethos, and a large menu; popular dishes include lobster soup, pecan-crusted oysters, wok seared shrimp, and pork schnitzel. The contemporary Marketplace Kitchen & Bar, with its brick and barnboard interior, also has a something-for-everyone menu, including vegan and gluten-free options. Start with appetizers like truffle frites or short rib empanadas, followed with entrees like the sesame-crusted tuna, lobster pappardelle, or the loaded vegan veggie bowl. For a quick bite on the go, you can’t beat the Woodbury Deli, serving hefty, freshly made sandwiches and wraps. They’re open for breakfast, too.
Antique shops, many housed in historic homes and buildings, line both sides of Main Street. It would take you days to browse them all, but the official Woodbury Antique Trail includes 15 shops and is a good place to start. One of our favorites is Wayne Mattox Antiques, housed in a circa 1835 Greek Revival home, filled to the gills with folk art, furniture, collectibles, and rare finds. Mattox, a well-known antiques expert, was a delightfully friendly ambassador, offering recommendations on other shops to visit, as well as things to do in the area. Other favorites we visited included Farmhouse Antiques, for casual farmhouse antiques and collectibles, and The Elemental Garden, specializing in rare garden antiques.
The 200-acre Van Vleck Farm and Nature Sanctuary and the 686-acre Whittemore Sanctuary both have a well-marked network of trails across farmlands and fields, along streams, and around ponds. The Nonnewaug Falls Trail offers great rewards for minimal effort. It’s an easy, less than a mile up-and-back hike through fields to a picturesque waterfall. The 78-acre or so town-owned Orenaug Park has rocky cliffs and a natural stone amphitheater. Walk the up-and-back trail to an observation tower with views of the Pomperaug River Valley.
Have you been to Hogpen Hill Farms? We were sitting at the bar at the 1754 House Inn, chatting with a friendly local. You must go, he told us. We’re glad we followed up on his recommendation. What we thought was a market or a local farm turned out to be an extraordinary sculpture park, featuring the whimsical, artful, large-scale work of artist Edward Tufte. Tufte is a pioneer in statistics and data visualization, a former professor at Princeton, professor emeritus of political science, statistics, and computer science at Yale University, author of five books on analytical thinking, and a sought-after consultant. That was his day job, but in 2006 he bought the farm, a 234-acre piece of land in Woodbury, to display his giant, beautiful artwork.
The ride down the long driveway is a clue to what you might discover. Tongue-in-cheek traffic signs read, “Art Is Art,” “And Everything Else,” “Is Everything Else.” And “If You See Something, Say Nothing.” Tufte invites visitors to simply slow down and enjoy, to look and see. That’s what we did.
A 12-foot long, aluminum cast fish entitled Magritte’s Smile, hangs above the entrance. From there, you can see artworks — more than 100 — located along a 1.5-mile diagonal, stretching across hills and valleys. We parked the car and strolled the grounds for up-close looks at the works: “Rocket Science 3,” a full-size, fully-equipped airstream with operating lights rocketing into air; Black Swan, a colossal, blow-up black swan floating in a pond; Stone Mountain, a field of colossal megaliths standing in the distance, and “Larkin’s Twig,” three-dimensional twig-like branches made of steel standing 322-feet high. One of our favorites was “Celestial Dancer with Calipers,” an elegant 84-foot-tall figure with blowing, wavy hair. She was beautiful.
“It’s funny and prankish and happy and pretty,” Tufte says of his sculpture farm. “Everyone who visits comes away smiling.”