Nine Funky Fall Road Races in Boston to Have on Your Radar

From an Oktoberfest 5k to crazy costume dashes, Boston has a pretty busy lineup of fall road races taking place in Cambridge to Fenway Park.

fall road races

Costume Dash / Photo provided

Take advantage of all the fall road races around the city, from costume dashes to the Reebok 10k for Women, before it truly becomes too unbearable to walk out your front door. We rounded up some of the funkiest ones, so put them on your calendar and lace up your sneakers.

Cider Donut Run: Sign up for this free fun run around Cambridge, either three miles or four, before loading up on the autumn essentials—cider donuts and adult beverages. Sounds like the perfect combination of things to us.

Free, September 27, 6:30 p.m., Marathon Sports: Cambridge, 1654 Mass. Ave. Cambridge,    

Reebok Boston 10k for Women: Join your daughters, mothers, sisters, friends, and colleagues for this special women’s only race that starts and ends near the Boston Common. The route goes along Beacon Street before turning onto Mass. Ave. to cross the river and will circle back for a complete 10k. If you’re not running, there are plenty of places to spectate.

$50, October 8, 12 p.m., Boston Common Parade Grounds,

fall road races

Reebok 10k for Women / Photo provided

Cambridge Oktoberfest 5K: What would fall be without celebrating Oktoberfest? And what would Oktoberfest be without beer and pretzels? First, circle around Kendall Square for a German-themed 5k (yes, people will wear their finest Oktoberfest outfits) and then head to the roof deck of CambridgeSide Galleria for Notch Brewing and Bantam Cider. Registration includes a pretty cool quarter-zip running shirt, three drink tickets, and fresh baked pretzels.

$45, October 7, 9:30 a.m.-1 p.m., CambridgeSide Galleria, 100 Cambridgeside Place, Cambridge,

fall road races

Oktoberfest 5k / Photo provided

The Great Pumpkin Dash: Summer may be over, but beach bashes totally aren’t. Revere Beach is hosting a fall market and pumpkin festival after a 5k race around Revere. Yes, costumes are encouraged and the best ones will receive prizes and giveaways. Festivities afterwards include pumpkin decorating, cookie decorating, and live entertainment.

$35, October 14, 9 a.m.-12 p.m., Revere Beach, Revere,  

fall road races

Revere Beach Fall Market / Photo provided

Head of the Charles 5k: Even if you’re not rowing in the Head of the Charles, it doesn’t mean you can’t pretend to be an athlete. Plus, racing right alongside the river while the boats are speeding through the water might just give you some extra motivation. The race will be lead by some local Fitbit Ambassadors, and you’ll have the chance to win the new Fitbit Charge 3.

Free, October 20, 9 a.m.-10 a.m., Community Rowing, 21 David G. Mugar Way, Boston,

Boston Costume Dash: Wear your best costume while you run through the city—just make sure you can see and move. As in, masks are probably not the best idea and heeled shoes better wait for the bar. Afterwards, the party continues in the Common with a costume contest and after-parties at a pub crawl from Barracuda to the Pour House.

$35, October 27, 9 a.m., Copley Square, Boston,

fall road races

Costume Dash / photo provided

Trick or Trot: There are no shortage of chances to show off your best group Star Wars costume or Dunkin’ Donuts (now, sans “Donuts”) get-up. If you’re busy during the Boston Costume Dash, head for this one that starts in Back Bay and benefits the Boston Road Runners.

Free, October 27, 9 a.m.-11 a.m., Capital One Cafe, 799 Boylston St., Boston,

Costumes for Cancer: Costumes are optional at this race around Chestnut Hill Reservoir. The short, 2.5-mile jaunt, or 5k if you want to take the loop around twice, benefits the John Estrella Foundation for Cancer Research. Each race participant will be able to enjoy a post-race trick or treat at local restaurants and bars in the area ranging from Cityside Bar to the Waterworks Museum and Pino’s Pizza.

$45, October 28, Chestnut Hill Reservoir, Boston,

Fenway Park Stadium Sprint: Race into previously closed off areas of Fenway Park in this two-day Spartan Sprint. You’ll be able to run through obstacles in the club house, down Landsdowne Street, and finish across home plate.

$130, November 10-11, 7 a.m.-7 p.m., Fenway Park, 4 Yawkey Way, Boston,