Middletown, CT

A lively Main Street on the Connecticut River

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About Middletown

Middletown is a small city on the Connecticut River in the center of the state, home to Wesleyan University and a walkable Main Street packed with restaurants, coffee shops and local stores. Homes range from downtown condos and historic houses to suburban neighborhoods and quieter, rural corners.

Quick Facts

  • Population: 47,717 (2020 U.S. Census)

  • County: Middlesex

  • School district: Middletown Public Schools

  • Getting around: Route 9 and Route 66, with I-91 nearby and the Arrigoni Bridge across the river to Portland

  • Setting: a small city with a historic downtown, suburban neighborhoods and some rural edges

Restaurants

  • Osa: a Main Street favorite for a special dinner out

  • Krust Pizza & Bourbon Bar: pizza and a big bourbon list

  • ION Restaurant: creative vegan dining

  • Fiore II Ristorante: classic Italian

  • MONDO: New York-style thin-crust pizza, paninis and pasta

Coffee Shops

  • Klekolo World Coffee: a local classic since 1994

  • Perkatory Coffee Roasters: specialty coffee roasted in-house

  • Perk on Main: coffee and sweet or savory crepes

  • Sweet Harmony Cafe & Bakery: baked goods and cafe fare

Shops

  • Main Street: dozens of local shops, restaurants and galleries in one walkable stretch

  • Wesleyan RJ Julia Bookstore: an independent bookstore right on Main Street

  • Adelbooks & More: used books and handmade gifts from Connecticut artists

Things To Do

  • Walk, fish or picnic along the Connecticut River at Harbor Park

  • Hike to the waterfall at Wadsworth Falls State Park

  • Catch a concert, lecture or art show at Wesleyan University

  • Bring little ones to Kidcity Children’s Museum

  • Spend an evening eating your way down Main Street

Thinking about buying or selling in Middletown? Let’s talk.

For more town data, see the U.S. Census Bureau’s QuickFacts and EdSight, the state’s school data site. Local business listings are my personal recommendations, not paid endorsements; please check hours before visiting.