Connecticut Local Events: Fall & Holiday 2026

Fairs, apple festivals, road races, parades and holiday lights around Greater Hartford and across Connecticut. We live and work here too, so we keep this list updated every week.

Updated October 5, 2026. 27 events. Dates come from each organizer’s page; confirm before you go.

Happening now

• Jun 14 – Oct 25: Blue Back Farmers' Market — West Hartford, Town Hall parking lot · Free
  Sunday farmers market, 10am-1pm; 2026 season ends October 25.
• Oct 1 – 31: Scarecrows Along Main Street — Wethersfield, Main Street, Old Wethersfield · Free
  31st annual display of more than 170 handmade scarecrows along Main Street, viewable sunrise to sunset.
• Oct 2–11: Southington Apple Harvest Festival — Southington, Southington Town Green
  57th annual festival over two weekends (Oct 2-4 and Oct 9-11) with food, crafts and rides.

October 2026

• Oct 9–11: Riverton Fair — Riverton (Barkhamsted), Riverton Fairgrounds
  Small-town country fair in the Litchfield Hills.
• Oct 10–11: Connecticut Garlic & Harvest Festival — Bethlehem, Bethlehem Fairgrounds
  Garlic-themed harvest festival with food, vendors and entertainment.
• Oct 10 – 25 (weekends): Connecticut Renaissance Faire — Lebanon, Lebanon Country Fairgrounds
  Weekend Renaissance faire, 10:30am-6pm, also open Columbus Day; ticketed admission.
• Sat, Oct 10: Eversource Hartford Marathon & Half Marathon — Hartford, State Capitol / Bushnell Park
  Marathon, half marathon, relay, charity 5K and kids run starting at the State Capitol.
• Oct 16–18: Glastonbury Apple Harvest & Music Festival — Glastonbury, Riverfront Park
  Three-day apple harvest festival with live music, rides and food.
• Sun, Oct 25: Donny's Dash 5K — Simsbury, Farmington River Valley
  Halloween-themed 5K, 1-mile walk and kids' run benefiting Boys & Girls Clubs of Hartford.

November 2026

• Sat, Nov 7: Run for the Riverfront 5K — Hartford, Riverside Park
  5K road race supporting Riverfront Recapture's parks.
• Sat, Nov 14: Hartford HealthCare Community 5K — Hartford, Mortensen Riverfront Plaza
  Community 5K run at Hartford's riverfront plaza.
• Sun, Nov 22: Stamford Downtown Parade Spectacular — Stamford, Downtown Stamford
  Giant balloon parade, noon-2pm, billed as the kick-off to the holiday season.
• Thu, Nov 26: Manchester Road Race — Manchester, Main Street
  90th Thanksgiving Day 4.748-mile road race on Main Street.
• Fri, Nov 27 (ongoing): Winterfest Hartford (rink opening) — Hartford, Bushnell Park · Free
  Free outdoor ice skating and skate rentals open for the season; closing date not yet posted.
• Sat, Nov 28: Santa Arrives by Tugboat & Lighted Boat Parade — Mystic, Mystic River Park · Free
  Santa arrives 2pm, tree lighting 6pm, lighted boat parade 6:15pm on the Mystic River.
• Sat, Nov 28: Simsbury Celebrates — Simsbury, Hopmeadow Street · Free
  Holiday festival with performances, firetruck parade and fireworks from Simsbury Meadows.

December 2026

• Dec 3–23: Lantern Light Village at Mystic Seaport — Mystic, Mystic Seaport Museum
  Ticketed holiday village experience on select December dates, 2-8:30pm.
• Thu, Dec 3: West Hartford Holiday Stroll — West Hartford, Blue Back Square / West Hartford Center · Free
  Free family holiday event with Santa, food and performances.
• Dec 3 – 13: Festival of Trees & Traditions — Hartford, Wadsworth Atheneum Museum of Art
  Annual fundraiser with decorated trees and holiday items on display throughout the museum; ticketed.
• Fri, Dec 4: East Hartford Annual Tree Lighting — East Hartford, East Hartford Town Green · Free
  Town tree lighting, 5:30-7pm.
• Dec 4 – 5: Bethlehem Christmas Town Festival — Bethlehem, Bethlehem town center
  Town festival with vendors, train rides, hayrides and a 5K road race.
• Sat, Dec 5: Norwich Winterfest Parade — Norwich, Downtown Norwich · Free
  Holiday festivities from 4pm with lighted parade at 6pm.
• Sat, Dec 5: River of Light Lantern Parade — Waterbury, Downtown Waterbury · Free
  Community-made lanterns paraded through downtown during Very Merry Waterbury.
• Sun, Dec 6: CLA Blue Back Mitten Run 5K — West Hartford, Blue Back Square
  Family 5K through decorated West Hartford neighborhoods; registration required.
• Sat, Dec 12: Carol Sing & Torchlight Parade — Windsor, Windsor Town Green · Free
  Carol sing and tree lighting at 6pm, then a parade of decorated vehicles and fire trucks.
• Sat, Dec 19: Wreaths Across America Ceremony — Middletown, CT State Veterans Cemetery · Free
  Annual wreath-placing ceremony honoring veterans, 12pm.
• Thu, Dec 31: First Night Hartford — Hartford, Bushnell Park / Downtown · Free
  New Year's Eve celebration in downtown Hartford.