Need a scenic, small-town escape filled with antiques and New England charm? Head to Woodbury! Known as Connecticut’s “Antiques Capital,” Woodbury offers rolling hills, colonial architecture, and peaceful countryside appeal. Whether you're treasure hunting, dining farm-to-table, or hiking forested trails, Woodbury delivers relaxed sophistication year-round.
Woodbury, CT Highlights:
- For Adventurous Travelers: Hike the trails at Flanders Nature Center & Land Trust – Explore forests, meadows, and wildlife habitats across beautiful preserves.
- For History Buffs: Step back in time at Glebe House Museum – Tour a Revolutionary-era home and gardens with deep colonial roots.
- For Shoppers: Browse antique shops along Main Street – Hunt for rare finds in dozens of charming antique and vintage stores.
- For Couples: Wine and unwind at Walker Road Vineyards – Sip local wines in a rustic, romantic tasting room setting.
- For Families: Explore Quassy Amusement Park & Lake – Enjoy classic rides, waterpark fun, and lakeside views just minutes away.
Best Time to Visit Woodbury, CT
The best time to visit Woodbury is in the fall (September–October) for peak foliage, antique festivals, and crisp outdoor adventures. Spring and summer are also ideal for hiking, wine tasting, and garden visits.
How to Get to Woodbury, CT
- If you are traveling by car: Woodbury is located along U.S. Route 6 and Route 64, about 45 minutes from Hartford and 1.5 hours from New York City.
- By Train: The nearest Metro-North station is in Waterbury, with car rentals or rideshares available for the 15-minute drive to Woodbury.
- By Plane: Bradley International Airport near Hartford is the closest major airport, approximately 1 hour away by car.
Where to Stay in Woodbury, CT
- Recommended for Families: Curtis House Inn – Historic inn with cozy rooms and onsite dining in a welcoming, family-friendly atmosphere.
- For Couples: Longwood Country Inn – Romantic 18th-century inn with fireplaces, canopy beds, and fine dining.
- For a Boutique Stay: The Milestone Inn – Simple, comfortable inn set along a scenic byway near town highlights.
Best Things to Do in Woodbury, CT
⮕ Flanders Nature Center & Land Trust
Hike peaceful trails and explore fun outdoor stuff with the family.
© Flanders Nature Center & Land Trust
Flanders Nature Center & Land Trust is a nature center and land trust that spans over 2,100 acres of open space across seven preserves in Bethel, Middlebury, Southbury, and Woodbury.
- Established in 1963 and located in Church Hill Road, the nature center aims to foster an appreciation and understanding of nature, art, and the wonders of the natural world through a variety of classes and workshops in art, nature and land preservation.
- The center also offers after-school and educational programs for adults, children, and youth groups, and summer camps.
- Facilities at the Flanders Nature Center include the Buz Russell Museum of Antique Tools and Farm Life, the North Barn, the Studio, the Trail House, the Sugar House, and the Natalie Van Vleck House.
Where You'll Find it: 596 Flanders Rd, Woodbury, CT 06798, Phone: 203-263-3711
⮕ Glebe House Museum & The Gertrude Jekyll Garden
Tour colonial rooms and admire romantic garden designs.
© Glebe House Museum & The Gertrude Jekyll Garden
Set in the historic center of Woodbury and surrounded by the picturesque Litchfield Hills, the Glebe House is a historic house museum on Hollow Road and one of earliest historic house museums in the nation.
- Built about 1740 in the Georgian colonial, the house was also the site of the first Episcopal Church election in the United States and is a significant architectural building.
- The house also features an incredible regional furniture collection and is surrounded by the Gertrude Jekyll Garden, a magnificently landscaped garden designed by famed English horticultural designer and writer Gertrude Jekyll in 1926 and featuring a classic English style mixed border and foundation plantings, and a planted stone terrace.
Glebe House Museum & The Gertrude Jekyll Garden, 49 Hollow Rd, Woodbury, CT 06798
⮕ Highwire Deer and Animal Farm
Feed friendly animals and enjoy an exciting day with the kids.
© Jeramey Lende/stock.adobe.com
The Highwire Deer and Animal Farm is a community farm that has been caring for injured and abandoned animals since 1982. The farm is home to a collection of exotic animals that visitors to the farm can enjoy interactive experiences with, touching and feeding them. Animals include a kangaroo, a camel, deer, donkeys, sheep, and a zebra and her baby Zeedonk (a cross between a zebra and donkey) and is only open Wednesday through Sunday during the summer months.
68 Park Rd, Woodbury, CT 06798, Phone: 203-263-4522
Activities and Attractions for Couples and Singles:
⮕ The Hidden Acorn
Shop rustic treasures and explore unusual vintage finds.
© The Hidden Acorn
The Hidden Acorn is a charming store on Route 47 in Woodbury that sells antiques, vintage furniture, home décor, and restoration products. The off-the-beaten-track gem in Litchfield County is part retail store; part refurbished, refinished, and restored furniture, part home goods store, and part art studio. Owned by Debbie and Andy Smith, who opened the store in 2017, the Hidden Acorn has an art studio where visitors can enjoy classes in the art of restoration, as well as arts and craft classes and workshops. The Hidden Acorn store is set within a barn built by Burton Judson in 1850 that was once a timber frame mill and has a charming rustic-workshop feel to it. In addition to selling a range of antique and vintage home décor, furniture, and housewares, the store also has an inventory of restoration hardware and refinishing supplies.
385 Washington Rd, Woodbury, CT 06798, Phone: 203-586-1223
⮕ Abrash Galleries
Browse antique rugs and admire affordable global art pieces.
© Abrash Galleries
Abrash Galleries
is a store on Main Street North in Woodbury that sells rugs and carpets and offers a wide range of rug services from washing and restoration to appraisals to design services. Owned by Karen Reddington-Hughes, the one-stop rug shop boasts a hand-curated selection of exceptional and high-quality oriental rugs sourced from around the world. The shop also offers services such as rug washing, rug restoration, rug appraisals, rug cushions, rug lectures and design services.
40 Main St N Woodbury, CT 06798, Phone: 203-263-7847
What to do if you are traveling with kids:
⮕ Quassy Amusement Park & Waterpark
Ride coasters and splash around during a summer family trip.
© Quassy Amusement Park & Waterpark
Quassy Amusement Park & Waterpark is a fun family destination that features a Splash Away Bay Water Park, a beautiful sandy beach, and a variety of fun-filled classic and newer theme park rides. Established in 1908 and located on the south shore of Lake Quassapaug in Middlebury, the family-friendly park boasts a vast family redemption arcade, an award-winning Wooden Warrior roller coaster, swimming at a lovely beach, a huge water park with more than 22 rides and slides, picnicking and a catering service for private parties. Once populated by Native Americans, the 20-acre area was bought by three Waterbury businessmen in 1937 and transformed into an amusement park with a carousel, paddleboats, a hot dog stand and a tearoom. During the late 1970s, rides were added almost every year and today also has its clambake facilities.
Rt. 64 (2132 Middlebury Road), Middlebury, CT 06762, Phone: 1-800-FOR-PARK or 203-758-2913
⮕ Charcoal Chef
Savor grilled favorites and enjoy an easy, classic weekend meal.
© Charcoal Chef
The Charcoal Chef is a family-friendly restaurant and Woodbury landmark that has been serving delicious homecooked food for more than 63 years. Established in 1956 by Robert Sanderson and his wife, Vee as a small drive-in that serviced long-distance truckers, the Charcoal Chef has expanded to a family restaurant that now seats over 100 people. Originally set up a 1950s-style diner, the restaurant served a menu that focused on charcoal-grilled meats. And still does so today. The menu features signature dishes such as Charcoal Broiled Hamburger with French Fries, Pickles and Cole Slaw, a Steak Basket of Charcoal Broiled Top Round Steak and French Fries; Steak Sandwich Served with French Fries and Chili Burger with Chili with Beans and Onion. The restaurant also serves a variety of craft beers, casual wines, coffee liqueurs, and handcrafted cocktails.
670 Main St N, Woodbury, CT 06798, Phone: 203-263-2538
⮕ Hogpen Hill Farms Sculpture Park
Wander through large-scale art and enjoy peaceful outdoor sights.
© lobro/stock.adobe.com
Hogpen Hill Farms Sculpture Park is part of Hogpen Hill Farms, a 234-acre landscape sculpture park and tree farm in Connecticut’s Litchfield County that features one hundred works of art created by Edward Tuft. The artwork in the park remains “open space in perpetuity.” Visitors pay for admission to Hogpen Hill Farms Sculpture Park by car and admission tickets include a map guide to the property, access to the sculpture barn, and parking. Guests are also welcome to have a picnic in the park. It’s also possible to drive-in to Hogpen Hill Farms without a ticket and pay when arriving.
100 Weekeepeemee Rd, Woodbury, CT 06798
If you are interested in local events:
- For Art & Food Lovers: Woodbury Fall Festival (October) – Celebrate fall with local food, music, crafts, and antique showcases downtown.
- For Families: Holiday House Tours (December) – Step inside festively decorated historic homes and inns.
- For Antiques Enthusiasts: Woodbury Antiques & Flea Market (Seasonal weekends) – Hunt treasures, vintage wares, and collectibles from dozens of vendors.
Day Trip Itineraries Within 30 Minutes of Woodbury, Connecticut:
- For Families: Quassy Amusement Park (20 min) – Classic lakeside fun with rides, waterpark slides, and family-friendly games.
- For Nature Lovers: Southford Falls State Park (20 min) – Hike to scenic waterfalls, picnic, or fish along woodland trails.
- For Couples: Litchfield (25 min) – Stroll historic streets, shop boutiques, or visit vineyards in this charming New England town.
- For Outdoor Enthusiasts: White Memorial Conservation Center (30 min) – Explore hiking trails, nature exhibits, and birdwatching in a vast preserve.
- For Garden Enthusiasts: Hollister House Garden (30 min) – Tour an elegant English-style garden nestled in the Litchfield Hills.
Frequently Asked Questions:
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Q: What makes Woodbury unique?
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A: Woodbury is unique in that the town is not nucleated and the older buildings are set linearly along both sides of a road that stretches for over a mile.
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Q: What historical significance does Woodbury have?
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A: The town’s National Register Historic District is home to several historically significant public buildings.
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