Run in Southeastern Connecticut Planning Region, Connecticut | 2026-2027

Hoo's Fooling Who 2 Miler [o2eventproductions.com] [Register at runsignup.com]
Sat, Apr 04, 2026 at 10:00 AM
Description
Join us for our 2nd Annual race, supporting the Oak Grove Montessori School.

No fooling, this will be a family fun 2-mile race.
- Fun race swag
- (Must register by March 2nd to guarantee swag)
*...
Join us for our 2nd Annual race, supporting the Oak Grove Montessori School.

No fooling, this will be a family fun 2-mile race.
- Fun race swag
- (Must register by March 2nd to guarantee swag)
- Division awards
- Custom race bibs
- Post race refreshments
- USA/TF Certified
- Music
- Professional chip timing
- Race managed by O2 Event Productions
- Race Time: 10:00 AM
- Bib pickup 8:00 AM to 9:45 AM
- Race Day Registration 8:00 AM to 9:45 AM
- Location: Horizons127 Babcock Hill Rd, South Windham, CT
- Racecourse map
2 Miles Run
127 Babcock Hill Rd, Southeastern Connecticut Planning Region, Connecticut, 06266, United States
OpenStreetMap Google Maps

FES PTO Chocolate Truffle Shuffle 5K Trail Run [runsignup.com]
Sat, May 02, 2026 at 9:00 AM

Description

Come run/walk/jog the 'sweet' trails of Giddings Park in Franklin, CT on 5/2, National Truffle Day! This chocolate truffle themed 5K race is open to all ages. (Dogs are welcome!) In addition to the...

Come run/walk/jog the 'sweet' trails of Giddings Park in Franklin, CT on 5/2, National Truffle Day! This chocolate truffle themed 5K race is open to all ages. (Dogs are welcome!) In addition to the all ages race, there will also be a "Mini Chocolate Chip" 800 meter (.5 mile) fun run for kids 12 and under. The kids fun run will start at 9:00am with the 5K Trail Run following at 9:30am. Bib pick up will be on race day only and is located at Giddings Park from 7:45am to 9:00am. Same day registration is available; credit card only. All 5K finishers receive a custom designed medal.

Register by 4/17/26 for early bird pricing of $30 for the 5K. After 4/17/26, price increases to $35.

5K course is three loops around the trails of Giddings Park with one large hill each loop. Total elevation gain is 235ft.

Awards for Overall Male and Female finishers. Additionally, prizes will be awarded for male and female age division winners.

Bib pick up and race location: 191 Pond Road, North Franklin, CT. Sponsored by the Franklin Elementary School PTO, Inc. All funds raised will support FES PTO's efforts for PTO-sponsored programs at Franklin Elementary School.

The 5K will be chip timed by The EMPIRE Timing Co.

5k Fun Run Run Trail Walk
191 Pond Road, Southeastern Connecticut Planning Region, Connecticut, 06254, United States
OpenStreetMap Google Maps
Bailey's Garden 5K [o2eventproductions.com] [Register at runsignup.com]
Sat, May 16, 2026 at 9:00 AM
Description
Bailey's Garden Foundation in Lebanon, CT, supports children with disabilities, founded by Jim and Mary-Grace Shifrin after losing their daughter Bailey, who had Trisomy 18, creating an accessible...
Bailey's Garden Foundation in Lebanon, CT, supports children with disabilities, founded by Jim and Mary-Grace Shifrin after losing their daughter Bailey, who had Trisomy 18, creating an accessible playground and providing grants.

Race details:
- Race Time: 9:00 AM
- Bib pickup 7:30 AM to 8:45 AM
- Race Day Registration 7:30 AM to 8:45 AM
- Location: Lebanon Green, CT170 West Town Street, Lebanon, CT
- Near the First Congregational Church
Race highlights:
- Race shirt
- (Must register by May 3rd to guarantee a shirt)
- Division awards
- Custom race bibs
- Post race refreshments
- Fast courseUSA/TF Certified
- Music
- Professional chip timing
5k Run
170 West Town Street, Southeastern Connecticut Planning Region, Connecticut, 06249, United States
OpenStreetMap Google Maps
Run the Vineyards - Jonathan Edwards 5K [gooddayforarun.com] [Register at runsignup.com]
Sun, May 31, 2026 at 9:00 AM
Description
Run for Wine at one of New England's most scenic and popular wineries- Jonathan Edwards Winery!

3rd Annual Run the Vineyards starts and finishes at this beautiful vineyard. This is a mostly paved...
Run for Wine at one of New England's most scenic and popular wineries- Jonathan Edwards Winery!

3rd Annual Run the Vineyards starts and finishes at this beautiful vineyard. This is a mostly paved race with a mile through the picturesque vineyard. Finish with wine, live music, food truck, beautiful views, and memories to last a lifetime. Fun for all ages and paces! Run the Vineyards races are unique, fun, and memorable traditions for families, friends, and running groups!

The Run:
- Chip-timed 5K race with instant results. Race starts at 9 AM.
- Scenic course finishing through the vineyard,.
- Awards for Top 3 Overall and Age Group Male & Female Winners (14 & under, 15-19, 20-29, every 10 yrs)
The Fun:
- Professionally managed 5K race and one-of-a-kind after-party
- All participants receive one complimentary glass of wine (21 and over)
- Post race Live Music 'til Noon by Bryan Titus
- Beer from Local Breweries also available for purchase
- Food Truck on site - Munchies Food Truck
The Extras:
- Run the Vineyards Stemless Wine Glass for all finishers
- High Quality Custom Tech Shirt included. Women's, Men's/unisex, and Youth sizes or upgrade to Women's Racerback Tank Top for $5 extra. Men's Tanks do not require an added fee. *Please register by May 17 to guarantee your first choice. Many extras ordered and available while supplies last after May 17.
- Souvenir Finisher Medal optional for $8 online or $10 race day
- Free Downloadable Race Photos. Professional Photographer on staff.
- Water Station on course, Water and Bananas at finish
- Walkers and children are welcome to participate.1 Hour time limit kindly requested. Need to be registered and start on time at 9 AM behind the runners for safety of all participants.
- Rain or Shine. No refunds or deferrals.
- Packet Pick-up on Race Day @ 7:30 AM - 8:30 AM at "Good Day for a Run" tent. Arrive by 8:30 AM to check-in please.
Volunteers receive glass of wine & free future race! Visit "Volunteer" Tab for details/sign up.

Invite Facebook friends on the Event Page here: facebook.com/events/2048866689182360
5k Run Walk
Southeastern Connecticut Planning Region, Connecticut, 06359, United States
OpenStreetMap Google Maps
Liz Harris Memorial Cannonball 1 Mile Run [runsignup.com]
Thu, Jun 18, 2026 at 7:00 PM

Description

Flat, fast certified 1 mile run. This race is a point to point race on a closed road.

1 Miles Run
Schoolhouse Road, Southeastern Connecticut Planning Region, Connecticut, 06365, United States
OpenStreetMap Google Maps

5 running events in Southeastern Connecticut Planning Region, Connecticut

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