Sometimes the best vacations are close to home, yet miles away in spirit. That’s exactly what Woodbury, Connecticut, offers— a delightful blend of New England charm, history, and modern comfort. Here’s your guide to the top things to do in Woodbury CT that will make your visit truly special.
Woodbury CT, and its bordering towns – Middlebury CT, and Southbury CT, the “Bury’s of Litchfield County – make up what is considered to be the region’s first established Antique Trail. Old colonial homes line Route 6 (Main Street), which was laid out along an ancient Indian trail when the town was established in the 1670s.
Main Street saw the advance of Generals Washington, Lafayette, and Rochambeau during the early struggles of our new nation. With one of the country’s only pewter factories and the country’s oldest inn, the town of Woodbury caters to travelers who yearn for an authentic “Colonial American” New England town experience.
But there’s more, including a family-owned lakeside amusement park, a mysterious Russian Village dating back to the 1920s, the birthplace of the US Episcopal Church, and a salt spa. So read on and come to the “bury’s of Connecticut.
Where Is Woodbury CT
Woodbury, Connecticut, is a charming town situated in Litchfield County, in the southwestern part of the state. About halfway between the cities of Danbury and Waterbury, Woodbury is approximately 90 miles north of New York City and around 40 miles southwest of Hartford, Connecticut’s capital. Known for its rich history dating back to the 17th century, the town is adorned with well-preserved colonial architecture and offers a range of antique shops, making it a popular destination for both history enthusiasts and collectors.
Looking for more weekeng getaway ideas? Here’s our roundup of romantic getaways in New England.
Things to Do In Woodbury CT
WALK: Flanders Nature Center
The 2,300-acre Flanders Nature Center is made up of six hiking preserves and nearly 50 Land Trust Parcels. The most well-known is the 200-acre Van Vleck Farm and Nature Sanctuary. Plan to stretch your legs on a 20-minute to one-hour loop that takes you through meadows, ponds, marshland and old forest – a diversity of habitats all in one place.
The 700-acre Whittemore Sanctuary is distinguished by a bog as well. The Nature Center was founded by Natalie Van Vleck (1901-1981), a single, never-married heir to the Macy’s Department Store fortune who dressed as a man and lived in Manhattan.
Van Vleck was passionate about art and traveled solo all over the world. She got into land conservation quite by accident – and oddly.
After winning a live turkey at a turkey shoot, she required land on which to keep it. So, Van Vleck purchased acreage up here and, in addition to turkeys, began raising prize-winning sheep. She bought more and more land as her flock grew. Since Van Vleck had no children, she left her property, plus some, to the community. Definitely worth a half-hour stroll.
SHOP: Mill House Antiques
Even if you aren’t particularly interested in old furniture, pay a visit to Mill House Antiques. A purveyor of fine 18th and 19th-century French and English pieces, the shop is set within the hunched, rough-hewn rooms of a 1700’s gristmill.
Mill House’s large “hatchet door” is so named due to its double-strength wooden planks laid both vertically and horizontally to prevent Indian hatchets from penetrating. Come in to smell the burnt wood from centuries-old fireplace fires.
VISIT: Glebe House Museum and Gertrude Jekyll Garden
Episcopalians and serious gardeners make pilgrimages to the Glebe House Museum and Gertrude Jekyll Garden. It is, after all, considered the birthplace of US Episcopal Church. This elegant and simple blue farmhouse is rimmed by the only authentic English Country Garden in the USA designed by famed British horticultural designer, Gertrude Jekyll.
The Glebe House is indubitably the most photographed building in the area. Plans for the garden were found in California in the 1980s, with flora replanted exactly to original specifications.
SHOP: Woodbury Pewter Outlet
One of the only pewter factories in the United States, Woodbury Pewter, sits right on Main St. Think Colonial-era kitchen, and these irregular matte-grey plates and mugs come to mind.
Though mostly a coach-bus-favorite gift shop now, you can watch artisans pour glistening molten pewter into molds.
Seeing this might invoke memories of required Middle-School reading, Johnny Tremain. A pewter apprentice, Temain botched a pour, melding his fingers into a fleshy web. Dangerous work.
VISIT/TASTE: Walker Road Vineyards
Walker Road Vineyards is a charming family-owned winery set amidst rolling hills and picturesque landscapes, the vineyard offers a tranquil setting for wine enthusiasts to explore. With a focus on sustainable farming practices, the vineyard produces a variety of wines, including reds, whites, and rosés, all of which reflect the unique terroir of the region.
Visitors can enjoy a leisurely stroll through the vineyard, partake in wine-tasting sessions, and even participate in harvesting events during the season. It’s an ideal spot for those seeking a relaxed wine experience in a bucolic setting.
SPA: Salt of the Earth Spa
Sit in a “salt cave” on a “zero gravity chair” and breathe in the health benefits of one of “three elements that create a life force for the human body.” (Besides water and light).
Surrounded by salt (granulated on the floor, infused into the air, and salt blocks walls), a 45-minute session at the Salt of the Earth therapeutic spa is purported to help alleviate sinus, allergy, and repertory problems, and quite possibly other ailments.
Things To Do In Middlebury CT
VISIT: Quassy Amusement Park – Middlebury CT
Scenically set on a lake, this small-scale, family-owned amusement park, three miles from Woodbury Center, has both dry and wet rides. The swoopy wood coaster, The Wooden Warrior, was rated among the Top 25 Wooden Roller Coasters in the world.
Spend hours on the beach, on super water slides, or watching your kids or grandkids have all the fun. It’s wholesome and small – you can’t get lost. Seasonal, so consult the website for hours.
Things To Do In Southbury CT
PHOTO OP: Bullet Hill School – Southbury
Built in 1789, The Bullet Hill School is one of New England’s oldest surviving brick schoolhouses. Earlier known as the brick school, it is thought to have acquired its name from a hill in Southbury where bullets were cast during the Revolutionary War. Classes were held here until 1941, and it is now used for local school programming.
STOP: Russian Village and St. Sergius Chapel, Southbury
Two Russian writers, Count Ilya Tolstoy, the son of Leo Tolstoy, and Siberian novelist George Grebenstchikoff established this slice of Russia in Connecticut in 1925. It was conceived of as an artistic community for those who fled to America after the Revolution of 1917. Visit, and the Russian Village calls to mind a fairy tale town hidden in the woods.
It’s unlikely that any descendants still live in this quaint, vaguely mysterious community (where every street is a dead end). Those who do live here dissuade tourists from ogling.
But you can still stop by to see the exquisite chapel that sits behind trees off to the left as you first enter the neighborhood. If it’s open, you can ask to see it. If not, take a picture and politely move on.
Woodbury CT Restaurants
EAT: 1754 Dining Room – Woodbury
After a change of owners, The Curtis reopened as the 1754 House under chef Michael Bates-Walsh, who knows how to tweak classic New England fare with panache.
EAT: Good News Restaurant
Locally sourced ingredients and an emphasis on farm-to-table dining make the Good News Restaurant a hit among both locals and visitors. Whether you’re craving a gourmet burger, a seafood delicacy, or a vegetarian treat, it’s got you covered. With its attentive service and cozy ambiance, it’s a must-visit spot for anyone seeking a memorable dining experience in Woodbury.
EAT: Locals also recommend
Market Place Kitchen and Bar, Carlito’s of Woodbury, and John’s Café, which has won over no less than jaded New Yorkers.
Woodbury CT Hotels
STAY: 1754 House – Woodbury
If all this antiquing and pewtering and eating is getting you tired, and/or if you’re in need of an inexpensive place to stay the night, book a room at 1754 House (formerly Curtis House).
Built as a home in 1736 and turned into an inn in 1756, it claims to be the Oldest Inn in Connecticut, but of course has been modernized to upscale standards.
STAY: Millstone Inn – Woodbury
Renovated roadside mom-and-pop motels are experiencing somewhat of a renaissance, and that goes doubly for this “inn.” Yes, it’s a motel, but with pillow-top beds, wi-fi, Keurig coffee makers, flat screen TV, and fine furnishings, it’s more “boutique” than “roadside.” And the price is so right.
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Love this! I live in southbury myself!