Top 9 Best Small Towns in Connecticut

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1. Greenwich

The largest town on Connecticut's "Gold Coast," Greenwich features superb arts and cultural attractions, including the Bruce Museum and four beaches along the Long Island Sound. Visitors can enjoy year-round festivals

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2. Stonington

Located in the southeast corner of the state, Stonington is a charming seaside village known for its mile-long beaches, historic seaside homes, and eclectic shops and boutiques. This picturesque town is also home to two top vineyards

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3. Washington

Washington, Connecticut, offers a small-town vibe with a vibrant cultural scene. Nestled against the backdrop of the Berkshire Mountains, the town boasts dreamy natural surroundings, including Lake Waramaug and the Shepaug River.

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4. Mystic

Beloved for its classic New England aesthetic, Mystic is set on the majestic Mystic River. The village is famous not only for the Julia Roberts film "Mystic Pizza" but also for its charming shops and major attractions like the Mystic Seaport

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5. New Canaan

New Canaan features an adorable downtown and notable arts attractions like Grace Farms and The Glass House. Grace Farms offers workshops, concerts, and more on its stunning 80 acres of publicly accessible landscape.

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6. Old Saybrook

One of Connecticut's oldest towns, Old Saybrook offers a wealth of historical and cultural sites, along with one of the state's most beautiful beaches. The Saybrook Point Resort & Marina, a family-owned, AAA Four Diamond-rated property

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7. Simsbury

Simsbury is the quintessential New England town, featuring a picturesque downtown filled with historic houses, fine restaurants, coffee shops, and small boutiques. The town is also home to Talcott Mountain State Park, one of the state's top hiking destinations.

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8. Westbrook

Nestled on the banks of the Long Island Sound between New Haven and New London, Westbrook is a quaint shoreline town with all the beachy amenities. Black Hall Outfitters offers water sports rentals, including canoes, kayaks

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9. Milford

Milford's charming downtown offers a variety of breweries, restaurants, and water views. The town's outdoor attractions include Silver Sands State Park, a public recreation space with beaches, dunes, restored marshland, and a 14-acre bird sanctuary.

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