Esquire magazine recently published a list of the best small town vacations in America. There’s something to be said for a glamorous vacation to a big city, but a small town trip can be just as delightful. One small town in Connecticut that made the list is Guilford. It may lack the pizazz of bigger cities like Hartford or Stamford, but there’s still plenty to see and do in this town of 21,000.

Fans of old architecture will be delighted by the streets of Guilford. The town has some of the oldest homes in New England. Many of the buildings date back to colonial times.
slack12/Flickr
The Henry Whitfield House, built in 1639, is the oldest standing house in Connecticut. The beautiful stone building was owned by Henry Whitfield, a Puritan minister. It's now a museum and open for tours.
Henry Whitfield State Museum, 248 Old Whitfield St, Guilford, CT 06437, USA
Swampyank/Wikimedia Commons
You can get more information about this historic home on the museum's website.

Address: 248 Old Whitfield Street, Guilford, CT 06437
Falkner Island is just off the coast of Guilford. The 2.87-acre island is part of the Stewart B. McKinney National Wildlife Refuge. It's home to a historic lighthouse that was commissioned by President Theodore Roosevelt.
Falkner Island, Connecticut, USA
U.S. Fish and Wildlife Service Northeast Region/Wikimedia Commons
Bishop's Orchards is a wonderful farm in Guilford that's been delighting residents for 150 years. This spot has a wonderful bakery and tons of locally-grown produce.
Bishop's Orchards Farm Market & Winery, 1355 Boston Post Rd, Guilford, CT 06437, USA
Bishop's Orchards Farm Market & Winery/Google Maps
Throughout the year, Bishop's Orchards hosts tons of great events, like you-pick-produce, live music, and a corn maze in the fall. You can check out a calendar of events on their website.

Address: 1355 Boston Post Road, Guilford, CT 06437

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Chatfield Hollow State Park just outside of Guilford is one of the most underrated state parks in Connecticut. It has 10 trails to explore, plus a water wheel, boardwalk, and covered bridge.
Chatfield Hollow State Park, Connecticut 80, Killingworth, CT, USA
Billandkent/Flickr
Get more information about this splendid state park here.
Fans of books won't want to miss Breakwater Books. This independent bookshop is in a cute area downtown.
Breakwater Books, 81 Whitfield St, Guilford, CT 06437, USA
Lisa M Annecharico/Google Maps
Find out more on their website.

Address: 81 Whitfield Street, Guilford, CT 06437
Looking for a bite to eat? There's plenty of spots in Guilford worth checking out. One that we love is Guilford Bistro and Grille Cafe. They've got a varied menu and it's all delicious.
The Guilford Bistro & Grille Cafe, 1016 Boston Post Rd, Guilford, CT 06437, USA
Cara Macdonald/Google Maps
Check out their menu on their website.

Address: 1016 Boston Post Rd, Guilford, CT 06437
This is such a beautiful little town to explore!
slack12/Flickr

Have you been to Guilford in Connecticut? Share your experiences in the comments!

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