Connecticut’s Favorite Shopping Towns Last Updated: November 2023

Part of Connecticut’s attraction has always been its small town centers, filled with personality, history, and charm. And what draws visitors, again and again, are the shops, boutiques, and artisans that reward browsers and buyers alike. Whether you’re planning a girls’ trip or looking for a great way to spend a day with family, here are a few of the towns around the state that have safely reopened and offer great shopping (and dining) districts.

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Lux and Local — Greenwich

Home to designer fashion boutiques and upscale shops, Greenwich Avenue in Greenwich has a neighborhood feel with a Rodeo Drive appeal, with local shops like Splurge sitting side by side with familiar names like Brooks Brothers and Vineyard Vines. Closer to the beach in Old Greenwich, you’ll find even more great shopping, like Back 40 Mercantile. Grab a bite between purchases at the Little Pub in Greenwich, or make a night of it at the stylish J House Greenwich

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Shoreline Sweet — Stonington Borough

The village of Stonington Borough is nestled in the heart of Stonington, Connecticut, just up the coast from Mystic. Here you’ll find quaint shops and galleries with unique gifts and one-of-a-kind treasures, from fashions and handcrafted jewelry at Indigo Bleu to the artisan appeal of The Velvet Mill. Replenish your shopping energy with dinner at the Water Street Café and make the trip last a little longer with an overnight at the Inn at Stonington.

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Antique and Artisan — Litchfield

In the northwest corner of Connecticut, you’ll find the town of Litchfield. Like nearby towns Goshen, Bantam, and New Preston, Litchfield is home to small local shops and restaurants. Shop for clothing at Serendipity Vintage & Handmade and sample baked treats at the Dutch Epicure Shop, a destination for foodies. Enjoy bistro-style lunch or dinner at the West Street Grill or sample handcrafted premium spirits at the Litchfield Distillery. And give yourself more time to explore the Litchfield Hills region with a night or two at the Hopkins Inn in nearby Warren.

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Outlet Style — Clinton

On the Connecticut shoreline, the town of Clinton’s version of a downtown shopping district can be found at Clinton Crossing Premium Outlets, a welcoming destination for designer bargains and more. You can also shop for classic antiques or kitschy treasures at Hey Day Antiques or find a dream wedding or bridesmaid gown at the famed White Dress by the Shore. In summer, grab a lobster roll at Lobster Landing. And for a taste of New England at the shore, stay at Sharlene Cottage.

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Suburban Sophisticate — New Canaan

In downtown New Canaan, the main shopping avenue is Elm Street. And that’s where you will find boutiques and restaurants for every taste and budget. Fuel up with a bite at elm Restaurant before taking on favorites like The Whitney Shop and Family Britches. After your spree, relax with a night at the Roger Sherman Inn and spend the next day visiting unique sites like the Glass House and the Silvermine Arts Center.

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Coastal Classic — Old Saybrook

Main Street in Old Saybrook is home to a lovely combination of coastal character and New England charm. From the Shops at Saybrook Country Barn, to Maximus Home, to Tova's Vintage and Old Saybrook Antiques Center, you’ll find an eclectic mix of shops and boutiques. Enjoy a meal at the neighborhood Penny Lane Pub, and be sure to make time for a stay at Saybrook Point Resort & Marina, located on Long Island Sound.

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Smart and Savvy — West Hartford

West Hartford Center is one of Connecticut’s best-known shopping districts, with everything from local boutiques to familiar names. Book a night at the hip Delamar West Hartford and you’re right in the heart of everything. Browse clothing, housewares and more at Hope & Stetson, find the latest fashions at Kimberly Boutique, or find the perfect gift at Ten Thousand Villages. Enjoy a meal or a drink on the rooftop deck of the Elbow Room, eat out on the patio at Zohara, or sample tapas at Barcelona. Afterwards, pick up a photo-worthy treat at Milkcraft or Donut Crazy.

You’ll find these and other great shopping destinations in Connecticut here.