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  • Writer's pictureLuckytheDuck

Here’s How You Can Vacation This Summer

There are summer towns that only come alive when the tide of tourists washes in from elsewhere, and then there are towns for summer that are already animated by local characters and a year-round lifestyle. Madison, Connecticut is one of those towns. For summer-seekers who prefer to blend into a shore town with an authentic life, Madison is the place. Four beaches on the eastern fringe of the town complete the summer vacation equation of charming town + rustic beach = New England getaway.

The Homestead bed and breakfast is a part of the authentic life of the town; the place has offered hospitality over 30 years and three generations of the same family. The property closed for safety in early March and has been preparing new cleaning procedures to go above and beyond recommendations from the CDC. The 10 rooms accommodate a maximum of 16 guests and the 13,000 sq. feet of indoor space, multiple outdoor decks and patios, all situated on just under two acres, provides plenty of space to spread out. Bonus, for beach goers it is an easy stroll or bicycle ride down to the Surf Club or one of the other under-the-radar beaches.

Madison, Conn. 101

When it comes to charming New England bona fides, Madison is legit. The roots of the town spread across four centuries and the Madison Historical Society makes it possible for you to explore architectural gems from three of those centuries via its mobile app walking tour. This ramble through history leads right to the heart of contemporary Madison where main street – Boston Post Rd – has charm, but it’s no movie set. This is a genuine commercial district that serves the locals even as it has adapted its colonial heritage and evolved to house the shop of an elite tea sommelier and one of the country’s best independent booksellers.

The Beach is within Reach

Go to the beach tops the list for many and the options here include Surf Club, East Wharf and West Wharf right along Madison proper. Hammonasset State Park is a local treasure with extended beachfront, multiple hiking trails through meadow, marsh and sand, and a nature center with programs for the entire family. And since nothing says summer like a good beach read, RJ Julia Booksellers is a natural complement. The staff of this shop specializes in helping customers find Just the Right Book and come what may, they are open virtually to keep up the matchmaking.

The Homestead team can recommend activities, but staff favorites include these beyond-the-beach options.

On the Road

Head out on a bicycle tour. Bring a bike or use one of the complimentary cruisers from The Homestead to explore town, assemble a picnic from the local cheese shop, delis or bakery and enjoy in the open air. You might motor a little further down the road to explore New Haven and its mix of ivy-clad charm, boutiques and pizza (the city is the trailhead of the Connecticut Pizza Trail). The Yale museums – Yale University Art Gallery, Yale Center for British Art, Peabody Museum of Natural History – are world-class and worth the trip. In fact, Connecticut has trails for most any passion including. The Antique Trail is extensive and includes open-air events like those on the Madison Historic Green, outdoor flea markets and established antique shops like the Clinton Antiques Center. There are also several options in the Clinton area for premium outlet shopping.

In the Woods

Take a hike for the fresh air and exercise and maybe a little history lesson to boot. Several Madison area trails wind through the ruins of early paper mills, iron bogs and sawmills. Chatfield Hollow State Park just outside of Madison has trails from easy to challenging and plenty of amenities to support a day of swimming, picnicking and more. The Guilford Land Conservation Trust has mapped multiple trails that wind through woods and rock fissures and along the remains of old colonial roads. More relaxing than remote is a wander around Lavender Pond Farm’s fields, pond and authentic covered bridge from master bridge wright, Arthur M. Graton.

On the Water

Lockdown ended and when the tide rise, get out on the water and cruise around The Thimble Islands, an archipelago of craggy islands, islets and frankly, just rocks populated by bold-face name summer residents. Kayakers have many options in the area from exploring the closer-in Thimbles to meandering the marsh and inlets of the coast or up a local river.

There are plenty of things to do in Madison and nearby towns along the shoreline, and many of them are of the off-the-beaten path variety like Duckpin Bowling – a deceptively tricky take on bowling – which is still played at vintage alleys in Conn. Antiquing, shopping, village green farmers markets and more can easily crowd a week but leave space between you and the next vacationer.

Where to Eat

It wouldn’t be a proper summer sojourn without fish shacks and that dining style spreads out by design. Local institutions in Madison include Lenny and Joe’s Fish Tale for gifts of the sea grilled, broiled, steamed and fried. The Clam Castle attracts its own devoted following for clam shack staples and classic summer fare. Café Allegre serves up real-deal Italian thanks to Chef Ilario Suppa, his father Silvio and probably his grandmother’s tutelage. The roots are deep, and authentic; ask for the cacio e pepe. Meriano’s Bakery and Cannoli Truck is worth a stop to finish a meal or celebrate a sunny afternoon. There is a lot of good food all along the Shoreline, start with these suggestions and ask around.

This may be a time of uncertainty about travel (be sure to check with businesses and attractions for current status), but it is certain that summer will come, and people will want to go on vacation. The good news is that restaurants, retail and accommodations have adapted so you can enjoy responsibly.

For more information on summer vacation in Madison, visit

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