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How to spend a perfect weekend in Connecticut

You can explore everything from pretty beaches to artsy downtown areas and Ivy League history in just 48 hours

Anni Irish |
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Trees outside on the green at Yale University Connecticut
Photograph: Supplied

When it comes to weekend getaways, don't rule out Connecticut. Boasting a gorgeous coastline with some of New England's best beaches, historic seaside towns, beautiful scenery and burgeoning food and arts scenes, the nutmeg state has something for everyone. Easily accessible by car or train from New York City, you can fit a lot into a single weekend in Connecticut. The country’s third smallest state can deliver art, great eats and much-needed time by the water, in just 48 hours. For a mix of culture, history and nature, base yourself in New Haven. The town is easily accessible by public transit, and has the perks of being proximate to one of the world’s most venerable colleges and by the seaside, all at once.

Diners eat by the water at Shell and Bones Connecticut
Photograph: Courtesy of Visit Connecticut

Friday evening

The best way to start your weekend in Connecticut is with some good old-fashioned New England seafood. Shell and Bones on New Haven’s waterfront offers a feast for your eyes and stomach. Preface your entrée with delicacies from the raw bar and classic New England clam chowder, wash it down with a glass of wine from their extensive list (just ask the staff for pointers if pairings aren’t in your wheelhouse). For your main course, consider the scallops or the Scottish salmon, or opt for the restaurant’s eponymous twist on surf and turf: Thai braised short ribs accompanied by BBQ jumbo shrimp.

Friday late night

Once you’ve had your fill of seafood, head to the cozy neighborhood joint simply called Bar. The name might be minimal, but these local favorites are consummate multi-taskers. You can sip craft cocktails or beer brewed on-site, listen to live music, bust a move on the dance floor or, if you’re still feeling peckish, order from their brick-oven pizza operation. Those hoping for a more relaxed atmosphere can visit the front room, which has an antique pool table and communal seating.

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Yale University Art Gallery Swartout and Street Hall Renovation
Photograph: Christopher Gardner

Saturday morning

There are a lot of things to do in and around Yale's campus. The Yale Art Gallery’s four floors house several exhibitions that change throughout the year and a diverse collection of art with more than 200,000 objects, including African and European art and contemporary works. It's one of the best museums in New England, and certainly the best value–entry is free.

Just a short walk from the gallery you’ll find streets of cute cafés and shops as well as the 16-acre downtown park New Haven Green. At the independent Atticus Bookstore, a New Haven institution that opened in 1976, you can browse titles, grab a coffee and find an unexpected literary treasure.

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A park in downtown New Haven
Photograph: Courtesy of Visit Connecticut

Saturday afternoon

Downtown New Haven offers a college-town vibe with an eclectic urban edge. With more than seventy shops, boutiques and restaurants, you’re likely to have a successful shopping expedition, no matter your style. Be sure to hit up Raggs, which stocks high-end, casual clothes for men and women from brands like Elizabeth and James, Frame Denim and Citizens of Humanity. If you like chocolate and jewelry (at once!)  then Wave Gallery is a hybrid shop that’s worth a visit.

Saturday evening

Top off a day of taking in the local sites with a great meal. Close to the New Haven Green, Basta Trattoria is a cozy Italian bistro that uses seasonal, locally sourced ingredients to turn out cult-favorite dishes. Be sure to try the restaurant’s famous meatballs, and pay special attention to their killer wine list. Capping off your meal with an espresso, a glass of sambuca and a piece of tiramisu is never a bad idea.

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Saturday late night

The nightlife in downtown New Haven is full of surprises. Take in several spots with a bar crawl. Start off at the Ordinary, a genteel, wood panelled bar that sits on the site of one of America’s oldest taverns. In fair weather, head to Elm City Social’s rooftop beer garden and finish the evening off with a live set at student favorite Toad’s Place, where you can catch a mix of local bands and touring indie acts.

Sheffield Island Lighthouse Norwalk County
Photography: Almdesign/Creative Commons

Sunday morning

An hour by train from New Haven, Norwalk is a quaint New England sea town. From the bustling downtown South Norwalk area (that’s SoNo to locals) to the Sheffield Island Lighthouse, there is a lot to see and do. From May to September, you can enjoy a ferry ride to the lighthouse, which was in operation from 1868 until 1902 and is now a museum.

Once on the island, you can visit the historic site, hike on waterside trails, birdwatch and take in the natural beauty of the Stewart B. McKinney National Wildlife Refuge. There’s even a weekly clambake on Thursday evenings during the summer months.  

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Sunday midday

Back in Norwalk, a short walk from the Sheffield Island Ferry, you can wander by cafés, restaurants and browse through shops. Grab a brew and a bite at Iron Brewing Company, or make a stop at the Sono Switch Tower Museum, a restored switch tower from 1896 that’s now a museum dedicated to railroads and their old mechanisms.

Lockwood Mansion exterior in Fairfield County, Norwalk
Photograph: Kindra Clineff

Sunday afternoon

Head further into the downtown area to stroll around the Norwalk Harbor. From the harbor, you can then take in some more local history with a visit to the Lockwood-Mathews Mansion Museum. This beautiful Victorian-style structure was built in the 1860s and today is a registered historical landmark that is open to the public. From here, make your way to the local favorite ice cream joint, Mr Frosty’s and treat yourself before your journey home.  

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