9 Boston Races to Look Forward to This Winter

A lone runner pulls ahead in Somerville's Jingle Bell 5K.
A lone runner pulls ahead in Somerville's Jingle Bell 5K. Blogger Little French Cat
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The light tap of measured steps, a rhythmic breath, the quiet burn in your muscles, a profound sense of mental calm—these are the qualities of some of the best runs. In stark contrast, every runner will also have runs where they never reach the Zen zone, and instead hit the dreaded "runner’s wall" long before the run is done. These are the times you wish for a bib and a nearby runner to hold you to a competitive pace. These are also the times when you remember how fun it is (and great for your PR!) to compete in a road or trail race.

From 5Ks to ultras, Boston and the greater Massachusetts area have you covered this winter. From now through January, plenty of races are being hosted throughout the state, and we’ve rounded up the best of them.

Holiday-Themed 5K Races

Holiday Fun Runs aren't the only times you can run in costume... but it's the one time you won't get funny looks for it.
Holiday Fun Runs aren't the only times you can run in costume... but it's the one time you won't get funny looks for it. Cambridge 5K Twitter

1. 5K Ugly Sweater Run
December 12, 2015—East Boston, MA

Don your scratchiest, ugliest, least sweat-wicking holiday sweater for this year’s Ugly Sweater Run. Amidst inflatable holiday decorations, photo stations, and holiday music, you’ll practically forget that you’re running a 5K altogether. If that isn’t convincing enough, runners receive a free knit hat, unlimited hot chocolate, and one beer after the race. Win! The race begins at 8:30am with the starting line at Suffolk Downs on William F. McClellan Highway. Registration costs $43.99 (with fees), with the option to donate to Save the Children. The much-deserved and incredibly hipster awards for best mustache, best fake mustache, best beard, and worst sweater are determined after the race.

2. Yulefest 5K
December 13, 2015—Cambridge, MA

Part road race, part Harvard Square block party, the annual Yulefest is a 5K/winter festival you don't want to miss. The race begins in front of Harvard Yard at 9:30am on a course that goes through the center of Cambridge and around Harvard. Post-race, three local breweries host a DJ dance party for all runners over 21-years of age. The race's $40 online pre-registration includes a knit hat and free food and beer at the after party.

3. 5K Jingle Bell Run
December 20, 2015—Somerville, MA

Featuring a winding loop course through Somerville’s quaint streets and a post-race party sponsored by Harpoon Brewery at 18 local hotspots, the 9th annual Jingle Bell Run in Davis Square has become a yearly favorite. At this race, you’re just as likely to encounter runners in full-blown holiday costume as you are to find them in techwear. Runners are encouraged to support the Somerville-based charity, Toys For Local Children, by donating an unwrapped toy or gift card to be given to a child in need this holiday season. Hosted by Somerville Striders Athletic Club, all participants receive a short sleeve t-shirt, a bottle-opener finisher medal, and a pair of jingle bells for their $37 entry fee. Early bib pick-up is available during race week and pre-registration is recommended, as the race typically reaches capacity. The race begins at 11am.

Races for a Good Cause

Boston runners brave a chilly 5K on a course through Somerville.
Boston runners brave a chilly 5K on a course through Somerville. Blogger Little French Cat

4. Boston Jolly Jaunt
December 5, 2015—Boston, MA

The final race of the Run to Boston Race Series, the Boston Jolly Jaunt, features holiday fun, prizes, and a flat 5K loop course that circles the Boston Public Garden, and takes runners up and down Commonwealth Avenue. By participating in the Jolly Jaunt, runners are supporting the series' fundraising goal of $175,000 to donate to athletes of the Special Olympics. Entry for this 9am race begins at $35 and increases to $40 on race day. Bib pickup is available on race morning and on December 4 from 3pm at the New Balance store on Boylston Street.

5. Miss Santa Holiday 5K
December 12, 2015—Boston, MA

Join runners along the picturesque Charles River Esplanade for the chip-timed Miss Santa Holiday 5K, which supports RACE Cancer Foundation and The Ellie Fund. The loop course is almost entirely flat, which also means fast. Runners begin the race at 11:15am and walkers at 10am at the Arthur Fiedler statue near the Hatch Shell. Race registration and a costume contest are scheduled for 9am and 11am, respectively. Cancer survivors may participate in the race for free, but all other runners must pay an entry fee of $25. An awards ceremony for top finishers and best costume will follow the race.

6. 7th Annual 5K Resolution Run to Kick Cancer
January 9, 2016—Lexington, MA

Sticking to your resolution to “run more this winter” is tough. Going through cancer is tougher. Join runners on this flat 5K loop course through historic Lexington as you support The Leukemia & Lymphoma Society (LLS), The American Cancer Society’s Making Strides Against Breast Cancer and the Floating Hospital for Children at Tufts Pediatric Hematology/Oncology.

The Annual 5K Resolution Run to Kick Cancer, which starts and ends at Lexington High School, begins at 11am, with registration and packet pick-up starting at 9am. Awards to the top three males and females, as well as the top three male and female cancer patients, are distributed in a ceremony at noon. Advance registration costs $30 while race day registration is $35. Advance packet pickup is available on January 8 from 3 - 7pm at Greater Boston Running Company in Lexington.

Going the Distance: 50K + and Triathlons

Running the TARC Fells Trail Ultra Winter race through a snowy Middlesex Fells Reservation.
Running the TARC Fells Trail Ultra Winter race through a snowy Middlesex Fells Reservation. Edith Dixon

7. TARC Fells Trail Ultra Winter, 32-40 miler
December 5, 2015—Stoneham, MA

The hardest of the hard run in this 32 to 40-mile, sunrise-to-sundown race through the rugged and scenic Middlesex Fells Reservation. Not only will this trail ultra test your endurance, but your technical footwork, too; plan to keep your eyes on the path as you dodge rocks, roots, and the fallen bodies of your competitors.

All warnings aside, this is one fun race. The course takes runners through 4-5 loops of The Fells’ roughly 8-mile Skyline Trail. Runners are required to attend a briefing at 6:45 a.m. sharp, and must have started the final loop on the 40-mile course by 2:30pm. Hosted by the Trail Animals Running Club, registration for this event is $22, and it often sells out. Have no fear, registration opens for next year’s run on January 1, meaning you have plenty of time to secure a spot (and train!) for 2016.

8. 18th Annual Fat Ass 50K Race
January 2, 2016—Topsfield, MA

“No fees, no awards, no aid, no wimps;” apparently that’s the motto for a Fat Ass 50K event. Only true masochists will appreciate a 50K in the Northeast in January. But some reports claim this year is supposed to be a fair weather winter, so even sane runners are encouraged to go the distance. With no race fee and no finish line awards, you’ll have to settle for the satisfaction of having run pretty darn far in one go.

The course is comprised of five 10K loops in Bradley Palmer State Park. Because 50K is no easy task, all runners — even those who participate in as little as one loop — are welcome to partake. Hosted by Gil’s Athletic Club, a local running club in Topsfield, the 18th Annual Fat Ass 50K Race begins at 9am at the eastern end of the state park. Detailed directions are available on the event page.

9. 6th Annual Latitude Indoor Triathlon Series: Race #1
January 23, 2016—Salisbury, MA

Hardened triathletes may scoff at the prospect of an indoor race. But those willing to journey south of Boston to participate in the first race of Latitude Sports Clubs’ Annual Indoor Triathlon Series will be happy they don’t have to swim the Charles River mid-winter.

The race consists of a 15-minute swim in a lap pool, a 25-minute bike ride in a spin studio, and a 20-minute run on the Club’s indoor track, with scoring based on the total distance covered. Athletes may compete in any singular race, a combination, or the full, three-race series. The second race will be held on February 20, 2016, and the third on March 5, 2016. Registration is from 9am to 11am. Race day cost is $40 for members, $50 for non-members, while pre-registration is $30 for members, $40 for non-members.

Know of an upcoming road or trail race in your community that we missed? Let us know in the comments.

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