10 running, road, swimming, and other events in Gloucester, Massachusetts

From big races to Saturday morning group runs—find running, road, swimming, and wheelchair events and connect with the local endurance sports community.

• Twin Lights Half Marathon [yukanrun.com] [Register at runsignup.com]
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  Sun, May 03, 2026 at 8:00 AM

  Description

  The Twin Lights Half Marathon offers a spectacular course with the seashore visible for much of the race's 13.1-mile route.

  YuKan is celebrating our 15th Anniversary in 2026! Run the twins and Save 15% on all both half marathons!

  13.1 Miles Half Marathon Run

  Gloucester, Massachusetts, 01930, United States
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• Twin Lobster [finishers.com]
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  Sun, May 31, 2026

  Half Marathon Run

  Gloucester, Massachusetts, United States
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• Twin Lobster Half Marathon [yukanrun.com] [Register at runsignup.com]
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  Sun, Jun 07, 2026 at 8:00 AM

  Description

  Enjoy beautiful ocean views along the coastline and run past the historic Fisherman's Memorial Statue.

  Run a scenic half marathon as you race along the spectacular back shore!

  13.1 Miles Half Marathon Run

  Gloucester, Massachusetts, 01930, United States
  OpenStreetMap Google Maps
• 2026 St. Peter's Fiesta 5K Road Race [raceroster.com]
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  Thu, Jun 25, 2026 at 6:30 PM

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  St. Peter's Fiesta 5K Road Race --- Thursday June 25, 2026 Race Starts 6:30 PM --- Run for a Reason: Your Support Makes the Difference Run for a reason. The Y is dedicated to ensuring everyone has...

  St. Peter's Fiesta 5K Road Race --- Thursday June 25, 2026 Race Starts 6:30 PM --- Run for a Reason: Your Support Makes the Difference Run for a reason. The Y is dedicated to ensuring everyone has access to our programming and services, from life-saving swim safety to youth development and childcare. Your registration supports this essential mission, ensuring we can continue to help those in our community who need the Y most. This year, your impact goes even further. We’re so excited you’ll be joining us for the 2026 Glen T. MacLeod Cape Ann YMCA St. Peter's Fiesta 5K Road Race. By participating, you’re not just running a race—you’re strengthening the foundation of Gloucester. Your commitment ensures that vital programs remain accessible to every neighbor, family, and child in our community. Get your running shoes ready! Looking for the ultimate way to participate in Gloucester’s annual St. Peter’s Festival celebration? This family-friendly course runs from Stage Fort Park right into the

  heart of the celebration. With fans lining the streets to cheer you on and a finish line right at the Fiesta Carnival, it’s more than a race—it’s a chance to celebrate our community and run for a life-changing mission. We can’t wait to see you at the starting line! --- Race Map --- Go the Extra Mile: Our Fundraising Levels Join our mission to provide financial assistance by reaching one of our meaningful fundraising levels! Every dollar you raise supports vital Y programs in our community. The Starting Line: Simply signing up supports our cause and starts the transformation! First Wave: Raise a total of $50.00. Harbor Bound: Raise a total of $100.00. Fiesta Champion: Raise a total of $250.00 or more to become one of our top champions! --- Race Day Details Race Start Time: 6:30 PM Location: Stage Fort Park, Hough Avenue, Gloucester, MA, USA Course Details: This course is stroller and dog friendly (well-behaved dogs only). Refund Policy: All sales are final, no refunds will be offered.

  Timing: Timing Provided by Bay State Race Services Swag: Tee Shirt first come first served while supplies last. Shirts must be picked up by the start of the race. Parking: Free parking is available at Stage Fort Park. Pre-Race Pick-up: Glen T. MacLeod Cape Ann YMCA. Tuesday 12:00–7:00 PM and Wednesday 8:00 AM–1:00 PM. Race Day Pick-up: Begins at 5:00 PM at Stage Fort Park. --- Results, Awards & Celebration * Results: Posted at the finish line and emailed to participants post-race. * Overall Winners: Medals for 1st Place Male & Female. * Age Groups: Medals for Top 3 Male & Female: 13 & under, 14–19, 20–29, 30–39, 40–49, 50–59, 60–69, 70+. * Open Categories: Medals for Top 3 Non-binary and Top 3 Wheelchair finishers. * Local Honors: Special prizes for the 1st Place Male & Female Gloucester residents. --- Quick Links & Resources Discover Cape Ann: Your guide to the local business community; find the best places to shop, dine, and stay in the region. Cape Ann Chamber of Commerce Discover

  Gloucester YMCA Member Resources: Our Y welcomes ALL. We strengthen communities, educate and nurture children, and promote healthy living in spirit, mind, and body. YMCA of the Northshore Upcoming YMCA Races and Community Events: Join us for Road Races, Golf Tournaments, Galas, and other Special Events! Fundraising and Community Events

  5k Road Run Swim Wheelchair

  Hough Avenue, Gloucester, Massachusetts, 01930, United States
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• Lone Gull 10K - 2026 [cccbsd.org] [Register at raceroster.com]
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  Sun, Sep 20, 2026 at 9:00 AM

  10k Run

  99 Thatcher Road, Gloucester, Massachusetts, 01966, United States
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• Around Cape Ann Half Marathon [yukanrun.com] [Register at runsignup.com]
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  Sun, Oct 18, 2026 at 9:00 AM

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  Since 1933, the Around Cape Ann Road Race has been a running tradition. Considered one of the best and oldest races in America, the Around Cape Ann Road Race is also among the most beautiful race...

  Since 1933, the Around Cape Ann Road Race has been a running tradition. Considered one of the best and oldest races in America, the Around Cape Ann Road Race is also among the most beautiful race courses in New England. The scenic course wraps around Cape Ann’s idyllic coastline and travels through the seaside villages of Gloucester and Rockport. The race provides spectacular coastal views of beaches, harbors and coves.

  YuKan is celebrating our 15th Anniversary in 2026! Register for the Six Pack Challenge and Save 15% on all six half marathons!

  13.1 Miles Half Marathon Run

  32 Cherry Street, Gloucester, Massachusetts, 01930, United States
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• Happy Holidays Half MerryThon & 5K Race [yukanrun.com] [Register at runsignup.com]
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  Sun, Dec 06, 2026 at 9:00 AM

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  Celebrate the holidays in sneakers!

  Bring the holiday cheer and run with the reindeer, elves and all the holiday friends! Enjoy beautiful ocean views as you run along the scenic coastline! Plus,...

  Celebrate the holidays in sneakers!

  Bring the holiday cheer and run with the reindeer, elves and all the holiday friends! Enjoy beautiful ocean views as you run along the scenic coastline! Plus, you’ll enjoy special holiday treats at the finish line celebration!

  Kids 5K race entry only $10.00! (ages 10-12)

  YuKan is celebrating our 15th Anniversary in 2026! Register for the Six Pack Challenge and Save 15% on all six half marathons!

  3.1 Miles 5k 13.1 Miles Run

  99 Thatcher Road, Gloucester, Massachusetts, 01930, United States
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