Day Trip Ideas: Wandering the Woodbury Antique Trail

Article written by Lee Elkins and updated by Liz Young.

Woodbury is the quintessential New England town, with its white-steepled churches, flag-lined Main Street and restored colonial homes. The beautiful town is a destination spot for antique lovers from all over the country.

One day is not enough to see all the shops that Woodbury has to offer, so before you go, check out a map and the Woodbury Antiques Dealers Association website to decide which shops match your interests. 

Main Street is divided into Main Street South and North, with the division occurring right in the middle of the northern historic part of town.

Moving north, you'll find another expansive barn called the Country Loft. Carole Winer has established her three-level shop as a source for French and American antiques, as well as a few reproductions. Country Loft has a romantic feel to it, with chandeliers and art hung beautifully throughout the post and beam structure.

Up on Main Street North tucked away behind a house is G. Sergeant Antiques. This shop is located in a picturesque barn with several rooms impeccably staged mainly with American and European pieces from the 17th, 18th and 19th centuries. The second level, with its soaring ceiling and decorative paneled wall, displays more furniture and art, as well as a collection of antique porcelain.

With so many shops to see, it can be overwhelming to narrow down your selections. Andrew Rowan of G. Sergeant Antiques offers three pieces of advice that the shop follows.

"We look for three things," Rowan said. "First, we make sure the piece is of the period it's representing. Next, that it is intact, with no major apologies [repairs]. And last, that the piece is distinctive in some way."

Rowan described antiquing as an intellectual pursuit.

"And it's a great way to pass on wealth to the next generation," he added.

The Food

Shopping works up quite an appetite. And next to being the antiques destination of Connecticut, Woodbury also has a fine foodie scene.

Dottie's Diner is farther south on Main Street and is famous for its doughnuts. The 1950s-style diner has booths and plenty of counter seating, where customers linger over coffee and the weekend paper. This restaurant serves traditional fare with a homestyle twist, such as banana walnut pancakes for breakfast and chicken pot pie with huge chunks of chicken and brown gravy. Go over the top for dessert with a slice of Dottie's chocolate or coconut cream pie, or the unique doughnut bread pudding.

Woodbury has more to offer than just antiques and tasty bites, so if you stay for more than a day, try to get out and enjoy the beautiful surroundings at Flanders Nature Center and Glebe House.