Boston Holiday Runs 2026 — Jingle Bell 5Ks & Santa Races

Bells on the shoelaces, cocoa at the finish: Boston's December calendar has 10 holiday-season races for 2026 — jingle bell runs, Santa dashes, and ugly-sweater 5Ks. They're the most beginner-friendly races of the year, built for families and first-timers. The next one up is 2026 Jingle Bell Run - Central MA on Sat, Dec 5, 2026. Every listing links straight to registration.

• Sat, Dec 5, 2026 2026 Jingle Bell Run - Central MA 112 Harding Street · Worcester, MA · From $35 5K Road
• Sun, Dec 6, 2026 Frosty Half-Marathon Raynham Middle School · From $65 5KHalf Marathon Road
• Sun, Dec 6, 2026 Jingle Bell Half Marathon & 5K 100 Elliott Street · Haverhill, MA · From $34 5KHalf Marathon Road
• Sun, Dec 6, 2026 Happy Holidays Half MerryThon & 5K Race 99 Thatcher Road · Gloucester, MA · From $29 5KHalf Marathon Road
• Sun, Dec 6, 2026 Winter Classic 5K 64 Sidney St · Cambridge, MA · From $40 5K Road
• Sun, Dec 6, 2026 Woo Jingle 5K and Kids Run (Race 1 Greendale Physical Therapy Worcester Triple Crown) Front St next to Worcester City Hall · From $15 5K Road
• Sat, Dec 12, 2026 Winter SOLEstice 5K Run/Walk 159 Church Street · Wilmington, MA · From $30 5K Road
• Sun, Dec 13, 2026 Bill Rodgers Somerville Jingle Bell Run & Walk Elm Street · Somerville, MA · From $30 5K Road
• Sun, Dec 13, 2026 Downtown Jingle 5K 11 Tidewater St · Pawtucket, RI · From $25 5K Road
• Wed, Dec 16, 2026 Raceday Certification 133 Leslie rd · Rowley, MA 5K Road

Race-day tip

December races are the best gateway race to give someone: register a friend, then train together through the cold weeks — accountability is the real gift.

Looking beyond december holiday? See every upcoming Boston race →