Settled back in 1639, Milford, Connecticut is a tight-knit, historic community that sits just 20 minutes away from both Bridgeport and New Haven. This small city has a classic New England feel thanks to its sprinkling of 18th-century homes and a downtown dotted with local stores, including the nearly 50-year-old gift shop, The Canvas Patch, and Scoopy Doo’s Ice Cream, which serves more than 80 flavors of ice cream, gelato, sorbet, sherbet and yogurts.

At the heart of the city is the Milford Green, said to be the second-longest green in New England. The 3.5-acre public space is the setting for cultural and recreational events throughout the year, like the annual Milford Artisan Market, which draws locals and visitors alike with live music, arts and crafts booths, and food vendors.

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Left: Stand Up Paddle-boarding in the sunset; Right: Sunset at the pier
Connecticut Office of Tourism

The city’s 17 miles of coastline offer ample opportunities for beach time and strolls along the boardwalks. And while its location on the Long Island Sound gives Milford plenty of natural beauty, locals also spend their time exploring nearby ponds, waterfalls and forests. Hiking trails connect every part of the 200-acre Eisenhower Park along the Wepawaug River, and the Connecticut Audubon Society Coastal Center has a wildlife refuge, bird sanctuary and year-round programming to entertain kids.