Connecticut fun runs
54 seasonal, themed and one-of-a-kind fun runs in Connecticut.
Holiday and seasonal: 20 · Food and drink: 15 · Costume and theme: 8 · Novelty course: 2 · Iconic tradition: 2 · Color, glow and night: 2 · Mud and obstacle: 2 · Quirky format: 2 · Animals: 1
- Novelty course Mohawk Mountain Race Connecticut's ski-area race: each 5K loop climbs Mohawk Mountain's ski trails to the summit twice during peak foliage.
- Costume and theme Middlesex Monster Dash 5K A Friday-evening Halloween 5K on a college campus, with trunk-or-treat, balloon animals and a DJ.
- Costume and theme All Hallows Eve 5K A late-afternoon Halloween 5K with a trick-or-treat stop at the halfway point, so runners carry a candy bag.
- Holiday and seasonal Ivoryton Pumpkin Chase A peak-foliage 'pumpkin chase' 5K that leaves the village's Main Street for a rocky, rooty trail loop along the Falls River.
- Animals Run & Wag 5K The region's signature run-with-your-dog 5K, through historic Cornwall Village and the Cornwall Valley in peak foliage season.
- Costume and theme Brookfield Halloween 5K and Kids Fun Run A 34-year-old town Halloween 5K past decorated houses, with costume prizes and leashed dogs welcome.
- Costume and theme Goodwill Halloween Hustle 5K and Walk Goodwill gives registrants 30% off at its stores to build a costume, then judges scariest, funniest and best group costumes at the race.
- Holiday and seasonal The Great Pumpkin Classic Running since 1991 on mostly its original course, with a post-race party of Plasko's Farm apple cider and pumpkin donuts.
- Costume and theme Andover Norton Commission Trick or Trot 5K Run/Walk The 'witches of Andover Lake' hand out treats along a lakeside 5K with adult, kid and group costume prizes.
- Holiday and seasonal HKYFS Pumpkin Run 5K, 2M & Kids Run A pumpkin-season road race with costume prizes and a community festival of vendors and activities.
- Costume and theme Collinsville Trick or Trot A Halloween-morning costume 5K on the Farmington River rail trail in the old mill village of Collinsville.
- Food and drink Lyman Orchards Pie Run A pie-themed Halloween-day race over the hilly orchards of one of Connecticut's best-known pick-your-own farms.
- Costume and theme Run for Your Life: Zombie Escape Road Race On Halloween morning, runners try to 'outrun the zombies' over a hilly 3K or 5K course in Watertown.
- Iconic tradition Tarzan Brown Mystic River Run A 51-year-old 5-miler with views along the Mystic River, ending in a post-race party at the Mystic Museum of Art.
- Food and drink Colony Grill 'Hot Oil' 5K A 2,000-plus-runner 5K named for Colony Grill's signature hot-oil bar pizza, starting from the pizzeria and already sold out for 2026.
- Food and drink Stonington Vineyards Wine Run Turkey Trot 5K A Thanksgiving-themed cross-country 5K looping through the vines of a founding Connecticut Wine Trail winery, with a medal that doubles as a wine stopper.
- Food and drink Hot COCO 5K, Walk & Kids Fun Run A late-fall 5K on the Farmington Canal Line that ends with a hot cocoa party.
- Iconic tradition Manchester Road Race presented by Hartford HealthCare One of America's oldest Thanksgiving runs (since 1927), where Olympians and costumed joggers share a 4.737-mile loop through downtown Manchester.
- Holiday and seasonal Run Santa Run Kids get to race Santa in a free fun run (bring a toy for Toys for Tots) before a Small Business Saturday 5K in downtown New Milford.
- Holiday and seasonal Jingle Bell Run Connecticut Arthritis Foundation holiday 5K where runners wear jingle bells and festive costumes.
- Holiday and seasonal NIA Jingle Bell Run A 38-year-old neighborhood holiday classic in Trumbull's Nichols section, with a costume contest and a Santa visit.
- Holiday and seasonal Santa Made Me Do It! A Santa-themed 5K run alongside Bethlehem's Christmastown Festival in the town nicknamed 'Christmas Town'.
- Holiday and seasonal Christopher Martin's Christmas Run for Children 5K A toy-drive 5K starting at a New Haven restaurant, credited with giving more than 60,000 toys to local children over the years.
- Holiday and seasonal Niantic Jingle 5K A holiday costume-contest 5K on a flat course along the Niantic shoreline that drew 1,400+ runners and walkers last year.
- Holiday and seasonal Roseland Park Christmas Run 5K & Kids Fun Run A Quiet Corner Christmas 5K with prizes for best Christmas costume and the first dog to finish.
- Holiday and seasonal New Canaan Santa Run A pre-Christmas Santa 5K that starts and finishes at the historic 'Castle' mansion in Waveny Park.
- Holiday and seasonal Frosty 5K Guilford's 41-year New Year's Day tradition loops past the town green, marina and fairgrounds, then serves hot clam chowder.
- Holiday and seasonal Cupid Made Me Do It 2 Mile Urban Challenge A 2-mile Valentine's race over three of Willimantic's bridges during the town's chocolate festival, with gourmet cupcakes for the winners.
- Holiday and seasonal Catch A Leprechaun 5K A St. Patrick's 'catch the leprechaun' 5K through the historic Connecticut River village of Essex.
- Color, glow and night Bubble Run Hartford Foam-cannon 5K at UConn football’s stadium with a bubble dance party at the finish.
- Holiday and seasonal Beach Bunny 5K A beach 5K on Easter weekend followed by Easter egg scrambles on the sand.
- Food and drink Black Hog Brewing Labor Day 5K A Labor Day weekend brewery 5K that ends with a post-race beer and live music at Black Hog Brewing.
- Holiday and seasonal Bob & Peg Andrulis Sweetheart Run & Walk Held on Valentine's Day itself, this 5-miler follows dirt and paved roads through the woods in the Litchfield Hills.
- Food and drink Boys & Girls Club of Milford Walnut Beach Ice Cream 5K A summer 5K on Milford's Silver Sands boardwalk where winners take home an ice-cream-bowl trophy and every finisher gets free ice cream.
- Novelty course Fight For Air Climb Hartford Connecticut's biggest stair climb: 688 steps and 34 floors up the Hartford 21 tower.
- Mud and obstacle Gaylord Gauntlet 5K Trail and Obstacle Run A homegrown obstacle race built by hospital staff on the 400-acre Gaylord Specialty Healthcare campus, with 24 natural and man-made obstacles.
- Food and drink Groton City Brew Run A waterfront 5K at Eastern Point Beach followed by a brew garden pouring from 18 Connecticut and Rhode Island breweries and distilleries.
- Holiday and seasonal John Demille Firecracker 8K Road Race A 60-year-old Independence Day 8K, one of Bethel's longest-running traditions.
- Food and drink Kelley's Pace National Donut Day Relay A free 4x400 donut relay on National Donut Day: each leg eats a donut, then runs about 400 m out and back.
- Food and drink Little Pub's Miles for Margaritas 5K A Cinco de Mayo-season 5K along Lordship's Long Island Sound seawall, with margaritas served at the finish.
- Food and drink Milford Road Runners Independence Day 5K A Fourth of July 5K from Tribus Beer Co. with a free beer and food at the brewery afterparty.
- Food and drink Mystic Pizza Run A running-store pizza crawl that stops at five Mystic eateries before returning to the shop.
- Color, glow and night New Milford Moonlight 5K An evening 5K along the Housatonic that kicks off New Milford's GOAT Days festival, with a baby-goat petting zoo and fireworks.
- Holiday and seasonal O'Hartford 5K and 10K (St. Paddy's 'O' Race Series) The finale of a four-race St. Paddy's series ends at midfield inside Trinity Health Stadium, with post-race New England Brewing beer.
- Quirky format Pirate's Beer Run! – A 0.5K Run For Cancer A deliberately absurd 0.5K (about a third of a mile, roughly seven minutes of walking) that ends in a beer and a donut.
- Food and drink Run the Vineyards – Jonathan Edwards 5K A mostly paved 5K with a mile through the vines at Jonathan Edwards Winery, finishing with a glass of wine and live music.
- Food and drink Run the Vineyards – Priam Vineyards 5K A 5K through a 40-acre estate winery that ends with a wine ticket, a stemless glass and live music.
- Food and drink Shore 2 The Pour Beach Run (Two Roads Brewing) Two Roads Brewing's roughly 3-mile race crosses the Audubon preserve at Stratford Point, then finishes on the sand along Long Island Sound with two beers.
- Mud and obstacle Sterling Down & Dirty 5K A local mud-and-obstacle fun run with 18+ obstacles at Stratford's Short Beach Park.
- Costume and theme Superhero Sunday Charity Race & Community Bash A superhero-costume 5K with superhero yoga warm-ups and a Kids Mighty Mile, raising money for Connecticut Children's.
- Holiday and seasonal Surfin' Santa's Christmas In July 5K & Holiday Stroll Christmas in July on the Long Island Sound shore, with Santa-themed runners, a kids' Elf Scamper and post-race 'Holiday Cheer'.
- Food and drink Taco Trials Eat a taco, run a one-mile loop, repeat ten times, starting from a Rocky Hill Taco Bell; throwing up means disqualification.
- Holiday and seasonal The Leprechaun Made Me Do It A 2-mile race held on St. Patrick's Day itself, run entirely inside Glastonbury's Riverfront Park and capped at 175 runners.
- Quirky format The Revolutionary Mile – At the Boom Box Parade A one-mile dash down the route of Willimantic's Boom Box Parade (marchers carry radios instead of a band) just before the parade steps off.