7. Crunch the leaves in a walk around Connecticut

Guilford: Experience 375 years of Guilford on foot. Pedestrians can learn the history of Guilford by walking on a free, guided tour given by volunteers. Tours are offered from mid-May until mid-October, which is the perfect time to peep at the leaves and peek at sites that are on the National Register of Historic Places. This tour is family friendly and a great way to teach children about the rich history of New England.

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Guilford’s calling card is one of the prettiest town greens in America. It’s also home to the third-largest collection of pre-Civil War homes in New England — but don’t pack your mothballs. Rows of tidy 17th-, 18th, and 19th-century dwellings stand facing dozens of shops, galleries, and eateries packed with designer duds and modern furnishings — with dashes of antiques thrown in. Past and present intertwine gracefully everywhere in town, from historic house museums to new waterfront mansions built on peninsulas reaching out into Long Island Sound.


Enthusiastic, knowledgeable guides lead two well-researched tours focused on Early American history and architecture. An extra treat: iPads loaded with historic photos. (Note: tours now start at the Information Kiosk, 32 Church Street, Guilford.)


Small New England Towns You Absolutely Need To Visit

From idyllic mountain villages to stunning seaside retreats, there’s just something special about life in small-town New England. Guilford is BuzzFeed’s #15 out of 24 small towns.

First organized in the 17th century, the town of Guilford is replete with reminders of its historic past. With many colonial and Victorian homes still standing, architecture is just one of Guilford’s charms. There are various trails and parks where visitors can take in the sights of the Long Island Sound, along which Guilford is located.

For hikers, Guilford is the promised land. There are numerous trails systems. The gateway to the New England National Scenic Trail is in Guilford. A hiker could arrive by train (Shoreline East) and easily walk to the gateway at the beach nearby.
Janet Ainsworth June 13, 2014


20 Unexpected Weekend Getaways to Plan This Summer

When you’re ready to peel yourself away, check out the Guilford Town Green, one of the country’s most pristine town greens, and home of a free walking or self-guided tour. In the summer, enjoy plenty of live theater and music or wander along the green’s many boutiques and restaurants.