Outdoor events near Gloucester, Massachusetts
32 outdoor events are on within 25 miles of Gloucester over the next three months: 29 races and 3 ranger-led or guided programs. One is this weekend. A typical October day in Gloucester reaches about 61°F and drops to 40°F, with rain or snow about 1 day in 3 (NOAA 30-year average).
- 32 upcoming
- 1 this weekend
- October: 9
- November: 17
- December: 5
- January: 1
- 5KFall Frolic 5K & Fun RunSun, Oct 11 · 9:00 AMLynch Park, Beverly · 11 mi from Gloucester
- Ranger programStar Party: AFTER-HOURS EVENTTue, Oct 13 · 7:00 PMRefuge - Parking Lot 1 · 14 mi from Gloucester
- 5KWoodville School Teddy Trot 5k Run/WalkSat, Oct 17 · 9:30 AMWakefield · 21 mi from Gloucester
- half marathonAround Cape Ann Half MarathonSun, Oct 18 · 9:00 AMGloucester · 0.7 mi from Gloucester
- RaceApple Harvest Run 2026Sun, Oct 18 · 11:00 AMWest Newbury · 19 mi from Gloucester
- RaceTopsfield Fall Foliage Classic Road RaceSun, Oct 18 · 11:00 AMTopsfield · 13 mi from Gloucester
- Guided tourParker River NWR Behind the Scenes Van Tour - WAITLIST ONLYSat, Oct 24 · 10:00 AMVisitor Center · 14 mi from Gloucester
- half marathon · 5KPortRun Half Marathon & 5KSat, Oct 31 · 8:00 AMRiverWalk Brewing Co., Newburyport · 16 mi from Gloucester
- 5KSpooky Sprint 5KSat, Oct 31 · 8:30 AMMelrose Family YMCA, Melrose · 23 mi from Gloucester
- half marathon · 5KOcean View Half Marathon & 5KSun, Nov 1 · 8:00 AMIpswich · 9.4 mi from Gloucester
- 5KThe Rotary Club of Marblehead 5KSun, Nov 1 · 10:00 AMCrocker Park, Marblehead · 13 mi from Gloucester
- Ranger programNovember Star PartyTue, Nov 3 · 6:30 PMRefuge Parking Lot 1 · 14 mi from Gloucester
- 5KCider Hill Farm 5K Fall RunSat, Nov 7 · 10:00 AMCider Hill Farm, Amesbury · 20 mi from Gloucester
- RaceHawk TrotSun, Nov 8 · 9:00 AMMelrose · 23 mi from Gloucester
- half marathon · 5KHarborside Half Marathon & 5KSun, Nov 8 · 9:00 AMNewburyport · 15 mi from Gloucester
- RaceWicked Kidz Fun RaceSun, Nov 8 · 1:15 PMGlen Urquhart School, Beverly · 11 mi from Gloucester
- RaceStoneham Veterans Day RunWed, Nov 11 · 11:30 AMStoneham · 23 mi from Gloucester
- 5KGNOCA 5K RUN/WALK IN HONOR OF JACKIE POOR AND PAULA HOLMSun, Nov 15 · 8:30 AMMichael's Harborside, Newburyport · 16 mi from Gloucester
- half marathon · 5KLivestrong at the Y 5K & Half MarathonSat, Nov 21 · 8:30 AMLt. Ross Memorial Park, Peabody · 15 mi from Gloucester
- 5KNOMAD Holiday Prelude 5KSat, Nov 21 · 10:00 AMWakefield · 22 mi from Gloucester
- RaceLynnfield Rotary Turkey TrotSun, Nov 22 · 8:30 AMLynnfield · 19 mi from Gloucester
- 5KWobble Before You Gobble: 5K and Kids' DashSun, Nov 22 · 9:30 AMMalden · 24 mi from Gloucester
- RaceWakefield Turkey TrotThu, Nov 26 · 7:30 AMWakefield · 21 mi from Gloucester
- 5KNorth Reading 5k Turkey TrotThu, Nov 26 · 8:00 AMNorth Reading · 21 mi from Gloucester
- 5K9th Annual Middleton Turkey Trot 5KThu, Nov 26 · 8:00 AMMiddleton · 17 mi from Gloucester
- 5KWill Run for Pie - Turkey Trot 5K Run/Walk (2026: NOW AT MAUDSLAY STATE PARK IN NEWBURYPORT MA)Thu, Nov 26 · 8:20 AMNewbuyport · 16 mi from Gloucester
- half marathon · 5KJingle Bell Half Marathon & 5KSun, Dec 6 · 9:00 AMHaverhill · 22 mi from Gloucester
- 5KHappy Holidays Half MerryThon & 5K RaceSun, Dec 6 · 9:00 AMGloucester · 2.5 mi from Gloucester
- 2 mile · 4 mile · 6 mileSanta's Toy Trot...2-mile, 4-mile, 6-mile Road Race & Elves Fun RunSun, Dec 13 · 9:45 AMMerrimac · 22 mi from Gloucester
- 5KFestivus 5K for AutismSun, Dec 13 · 10:00 AMFinz Seafood & Grill, Salem · 13 mi from Gloucester
- RaceMystic Runners Santa Dash ClassicSat, Dec 19 · 10:00 AMLakeside Inn, Wakefield, MA, Wakefield · 21 mi from Gloucester
- 5K · 10KWCRC New Year's Day Hangover Classic: 5k, 10k, Plunge!Fri, Jan 1 · 11:30 AMSalisbury · 18 mi from Gloucester
More in Massachusetts
Schedules come from park agencies, race sites and organizers' own calendars, checked daily. Events can change, so check the event page before you go. Typical weather is the NOAA 1991–2020 average.
