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Middletown, CT | 70 Main Street, Middletown, Connecticut 06457

Annual Middletown Events & Festivals

From fall fairs and celebrations to summers spent taking in concerts and music series, the Inn at Middletown is a gateway to everything going on in and around town. Plan a visit during the holidays and be a part of the tree lighting on the green, or stroll the Holiday Bazaar at Wadsworth. The spring season brings with it the Meriden Daffodil Festival and Daffodil Day at Wadsworth Mansion. Explore unique creations at the International Festival of Arts and Ideas, or uncover rare finds at Antique Cruise Night on Main. Middletown is a charming city where some of the region's best events take place year-round.


  • New Year's Day at Wadsworth Mansion


  • Connecticut Flower & Garden Show
  • Wadsworth Mansion Wedding Show
  • Eagle Watch at Riverquest Cruise


  • St. Patrick's Day Parade (Hartford and New Haven)
  • Easter Brunch at the Inn
  • Friends of Long Hill Tea at Wadsworth Mansion


  • Daffodil Day at Wadsworth Mansion
  • Meriden Daffodil Festival
  • Harvard Pilgrim Healthcare Middletown Half Marathon


  • Wesleyan University Graduation
  • Memorial Day Parade on Main
  • Mother's Day Brunch at the Inn


  • Connecticut Trails Day
  • Antique Cruise Night on Main
  • International Festival of Arts and Ideas
  • Elizabeth Park Rose Weekend
  • TPC River Highlands Travelers Championship Golf Tournament
  • 18 Hole Stroll for Pancreatic Cancer


  • Music at the Mansion Summer Series
  • Riverfest 4th July Celebration
  • Middletown 4th of July Fireworks
  • Citizens 5K on Main
  • Greater Hartford Festival of Jazz
  • Craft Expo
  • Deep River Ancient Muster & Parade


  • Open Air Market & Festival at Wadsworth
  • Motorcycle Mania
  • Dragon Boat and Asian Festival
  • Sunflower Maze at Lyman's


  • Discover Hartford Bicycle and Walking Tour
  • Durham Fair (New Haven)
  • Civil War Day at Middlesex Historical Center
  • Corn Maze at Lyman's Orcharf
  • Berlin and Portland Fair


  • Haunted Halloween Party at Wadsworth
  • Halloween Party on Main
  • EverSource Hartford Marathon
  • Octoberfest at PowderRidge
  • Halloween at EmPower


  • Tree Lighting on the Green
  • Family Thanksgiving Dinner at the Inn


  • Holiday Bazaar at Wadsworth
  • Holiday on Main Street
  • Brunch with Santa at Lyman's
  • New Year's Eve on Main
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