Six Festive Holiday Fitness Events in Boston to Check Out

Heartbreak Hill Running Co. Jog and Nog / photo provided

During the holidays, it might be easy to forget about the gym, especially when there are cookies to be decorated, presents to be wrapped, and a turkey to be trimmed. Fortunately, you can bring the festive fun to your workout, instead of hammering away in the gym, during one of these holiday fitness events in Boston. Just be sure to come dressed in the spirit of the season with a jolly demeanor—no one likes a Scrooge.

1. Miss Santa Holiday 5k

Hit the Esplanade for this flat and fast holiday race, and get the chance to win best “Miss Santa” costume. Afterwards the fun continues at Fire + Ice for a post-race after-party. Be sure to register in advance, as tickets go up $15 day of.

$25, December 7, 11 a.m., DCR Hatch Shell, 47 David G Mugar Way, Boston, racecancer.org. 

Santa Speedo Run / Photo provided

2. The Santa Speedo Run

This Boston tradition began 20 years ago with five guys looking to spread some holiday cheer running through Back Bay in nothing but Santa hats and speedos. Fast forward to this year, when the race will celebrate its 20th anniversary, and it has grown to raise nearly $2 million for local children in need. You’re encouraged to dress in your most cheerful attire (speedos aren’t required). The course is only a mile long down Boylston Street with an after party at Back Bay Social Club.

$30, December 14, doors open at 10 a.m. and the run starts at 1 p.m., Back Bay Social Club, 867 Boylston St., Boston, ssrun.securesweet.com.

3. Cambridge 5k Yulefest

If you’re one of those people who enjoy signing up for races just for the afterparty and the swag, this Harvard Square 5k is for you. Each participant receives a Yulefest winter hat and admittance to a post-race block party with local brewers Bantam, Notch, and Slumbrew.

$45, December 15, 9:30 a.m.-1:30 p.m., Harvard Square, 41 Church St., Cambridge, eventbrite.com. 

Jingle Ride / Photo provided

4. Ciclismo Classico Jingle Ride

This festive 22-mile ride follows the Minuteman Bikeway to Harvard Square, the Esplanade, Boston Common, and finally Newbury Street. It’s one of the longest-running holiday events in Boston and sure to be a cheerful endeavor for all those who participate. There’s even a pitstop with cookies and hot cocoa to warm up and refuel.

$25 encouraged donation to Horizons for Homeless Children/free, December 15, 10:30 a.m.-2 p.m., Kickstand Cafe, 594 Massachusetts Ave., Arlington, eventbrite.com. 

5. Jog and Nog

Join Heartbreak Hill Running Company for a fun run to see the lights in the South End and Lincoln Park neighborhoods, followed by a holiday party back at the shop. All runners are welcome for the 3-4(ish) mile run.

Free, December 19, 6:30 p.m., Heartbreak Hill Running Company, 652 Tremont St., Boston, jognog.splashthat.com. 

6. Happy New Year Day Ride 

Start your New Year off with a pleasant (and hopefully sunny) ride through downtown Boston. This bike ride starts in the Common and hits sights from Charlestown to Castle Island in a 20-mile trek.

Free, January 1, 11 a.m., Boston Common, 139 Tremont St., Boston, facebook.com.