Boston Halloween Runs 2026 — Costume 5Ks & Spooky Races

Costumes at the start line, candy at the finish: Boston has 23 Halloween-season races on the 2026 calendar, from pumpkin runs to full costume-contest 5Ks. Most award prizes for the best outfit — check each listing's organizer page for contest rules. The next one up is 7th Annual OLV Trick or Trot 5K on Sat, Oct 17, 2026. Every listing links straight to registration.

• Sat, Oct 17, 2026 7th Annual OLV Trick or Trot 5K 77 Mendon St · Uxbridge, MA · From $30 5K Road
• Sat, Oct 24, 2026 Womp Romp Wompatuck State Park - South Field · Norwell, MA Trail Run Trail
• Sat, Oct 24, 2026 BCNC's Family Fun Run & Walk Merrymount Park · Quincy, MA · From $25 5K Road
• Sat, Oct 24, 2026 Pumpkin Pacer 5k @ White Barn Farm White Barn Farm · Wrentham, MA · From $30 5KTrail Run Trail
• Sat, Oct 24, 2026 Wayside Youth & Family Support Network 5K4Kids 48 Frost Street · Framingham, MA · From $35 5K Road
• Sun, Oct 25, 2026 Canton Fall Classic 1301 Washington Street · Canton, MA · From $15 5K10K Road
• Sun, Oct 25, 2026 Powisset Farm Trail Run - Fall 37 Powisset Street · Dover, MA · From $20 5KTrail Run Trail
• Sun, Oct 25, 2026 27th Annual Flutie 5K for Autism presented by Eastern Bank Natick High School · From $8 5K Road
• Sun, Oct 25, 2026 Boston Purple Pumpkin 5K and Walk 1255 Soldiers Field Road · Brighton, MA · From $35 5K Road
• Sun, Oct 25, 2026 Clocker Club 5k Fundraiser 87 W Union St. · Ashland, MA · From $10 5K Road
• Sun, Oct 25, 2026 Esplanade 5K Run & Walk Fiedler Field · Boston, MA · From $35 5K Road
• Sun, Oct 25, 2026 Scaredy Cat K95K 200 Westboro Road · North Grafton, MA · From $35 5K Road
• Sun, Oct 25, 2026 Second Annual Run to Remember Brandi Stadium Drive · Nashua, NH · From $35 5K Road
• Sun, Oct 25, 2026 HCA Wicked 5K 2026 98 Hayden Rowe St · Hopkinton, MA · From $10 5K Road
• Sun, Oct 25, 2026 Move for MDS: Boston 1 Charles St · Boston, MA 5K Road
• Sun, Oct 25, 2026 The Baystate Dirty Dog Trail Run-Ruck-Walk 5k Across from 41 Point St · Berkley, MA · From $5 5KTrail Run Trail
• Sun, Oct 25, 2026 Run for the Hills 115 Prospect Hill Rd · Harvard, MA · From $15 5KTrail Run Trail
• Sun, Oct 25, 2026 Winky Providence Monster Dash 5K 250 South Water Street · Providence, RI · From $17 5K Road
• Sun, Oct 25, 2026 29th Annual Lawrence Vietnam Memorial 5k Run or Walk 652 Andover Street · Lawrence, MA · From $25 5K Road
• Sat, Oct 31, 2026 Spooky Sprint 5K Melrose Family YMCA · From $30 5K Road
• Sat, Oct 31, 2026 Cambridge Half Marathon + 5K 100 CambridgeSide Place · From $45 5KHalf Marathon Road
• Sat, Oct 31, 2026 Live Free Animal Rescue Franken Paws 5K / Walk Fundraiser 20 Rockingham Rd · Londonderry, NH · From $45 5K Road
• Sat, Oct 31, 2026 GET Fit Halloween 5k GET Fit · Bridgewater, MA · From $20 5K Road

Race-day tip

Test-run your costume BEFORE race morning. Capes tangle, masks fog, and inflatable dinosaurs add about two minutes per mile.

Looking beyond halloween? See every upcoming Boston race →