Connecticut's Coast Hides This Scenic City With New England Charm, Lively Arts, And Delectable Eats

Tucked along the Long Island Sound, Milford, Connecticut, marries centuries-old charm with modern-day vibrancy. The coastal city was founded in 1639, when land was purchased from a local Native American leader and settled by colonists thereafter. Not only is Milford the sixth-oldest town in the state, but it also lays claim to the second-longest town green in New England — Milford Green. Marvel at charming colonial homes lining the streets. Admire downtown's preserved architecture, boutique shops, and waterfront views. And with various parks waiting to be explored, Milford is ideal for nature lovers.

History buffs will find plenty to nerd out on. The Milford Historical Society maintains three beautifully preserved 18th-century homes set beside scenic Milford Harbor. The Eells-Stow House, listed on the National Register of Historic Places, is thought to be the oldest home in Milford and one of the oldest surviving homes in Connecticut. The Clark-Stockade House was begun around 1659 but dismantled in 1780, with the present-day home built in its place. Inside you'll discover period furniture, among other neat artifacts. Also dismantled and rebuilt as you see today is the Bryan-Downs House, which boasts an interesting Native American collection.

Learning about the city's key Revolutionary War landmarks and events further enriches the experience. For example, the Soldiers Monument in the Milford Cemetery commemorates 200 victims of smallpox whom the British captured and later released. Fort Trumbull, which was destroyed in a 1781 attack led by infamous traitor (and Connecticut's own) Benedict Arnold, was built to safeguard the region. The city's location is enviable. Milford's proximity to the quiet beach town of Guilford means sunbathing is always within easy reach. And with Tweed New Haven Airport about a half-hour's drive away, getting here is as smooth as the pace of life.

After setting off on a paddle-powered cruise through the harbor and Long Island Sound — with stellar views of Charles Island and the surrounding coastline — it's time to immerse yourself in the arts. Milford's artistic spirit is alive and well, thanks largely to the Milford Arts Council (MAC). Founded in 1972, it has transformed the town's former train station into a thriving cultural hub. You can catch everything from theatrical performances and indie concerts to community workshops and visual art exhibits. The MAC's Firehouse Gallery, housed in a historic firehouse, showcases local artists and offers workshops, classes, and pop-up events that drive community engagement. More than just performance spaces, these gathering places are spectacular venues that cultivate creativity and connection. 

Milford's arts calendar is jam-packed with annual events. The Eastbound Theatre stages three full-stage productions each year and a two-weekend original short play festival every summer. Don't miss riveting outdoor performances like Shakespeare in the Park. Classic and contemporary stories come to life here in a community-centered setting, reflecting Milford's firm commitment to fostering an appreciation for the arts. Additionally, the Milford Public Library hosts events like "Acts in the Stacks!," which pairs live theater performances with light eats and drinks, all for a low fee of $50. It's also a great place to simply unwind after a busy day of sightseeing. 

The annual Sand Sculpture Contest at Walnut Beach allows people of all ages to channel their creativity into crafting whatever they please. Anything from sharks and dogs to helicopters and spaceships is fair game! Whether you're a seasoned art lover or a curious newcomer, Milford might very well remind you of Burlington, a vibrant city between Chicago and Milwaukee with charming streets and a thriving arts scene. 

No visit to Milford is complete without delighting your palate. Milford's location along the Long Island Sound means fresh seafood is always on the menu. The Connecticut-style lobster roll — served warm and drenched in butter — was believed to have originated in Milford in the 1920s at Perry's Restaurant. Today, lobster rolls, along with other favorites like clam chowder and oysters, can be had at restaurants like The Lazy Lobster, which, according to a Tripadvisor reviewer, serves "the best lobster roll ever;" 7 Seas Restaurant & Pub, which was voted "Best Neighborhood Restaurant" by Connecticut Magazine between 2011 and 2013; and the Stonebridge Restaurant, whose signature shrimp cocktail is a definite crowd-pleaser. 

The annual Milford Oyster Festival , a revered tradition since 1975, is a highlight of the summer, drawing thousands to the waterfront for live music, artisan vendors, and, of course, locally sourced oysters. At the 2024 festival, a whopping 30,000 oysters were cracked open and savored. If you're not big on seafood, Milford's culinary landscape includes everything from rustic American comfort food to upscale international fare. Founders House Pub & Patio, located on the historic Milford Green, also serves up delicious steaks and burgers in a welcoming atmosphere. And just a 30-minute drive away is New Haven, "The Pizza Capital of the US," with exceptional eats of its own. 

Simply want a snack or cup of coffee to keep you going? Scratch Baking on the Milford Green offers a slew of baked goods and pastries. Just a few blocks away, Café Atlantique serves up crepes, paninis, and espresso drinks in a relaxed ambiance. You can also sample the region's flavors at the Downtown Milford Farmers Market, open every Saturday from June through October.