Three Destination Races to Escape the Cold

Way down near the southernmost tip of the U.S. stretches the scenic Florida Keys Overseas Heritage Trail. Featuring stunning Atlantic Ocean views, this trail’s genesis is surprisingly recent. The trail was designated a National Recreation Trail only in 2004. In fact, the 106-mile paved trail is still being completed; it will eventually connect Key Largo to Key West for travelers who want to explore the Florida Keys separately from travel on U.S. Highway 1.

Key West Half Marathon
What better way to experience this unique greenway than by running it? If that’s your first thought, look no further than the incredibly panoramic Key West Half Marathon, over half of which takes place on the Florida Keys Overseas Heritage Trail ( It also races through Key West’s historic Old Town district.

This half, which annually now has about 4,000 finishers, is one of many upcoming in 2017 that can be accurately described as destination races, a growing phenomenon that organizes vacation planning around road running events in one-of-a-kind places, for not just maximum fitness while traveling, but unique experiences that people may only discover because such events exist to induce them to visit in the first place.

Taking place on January 15, 2017, the Key West Half Marathon is in its 19th year. If you’re not quite up to speed to cover the 13.1-mile course, there is also the Hemingway 5K Sunset Run. Despite the name, the gun immediately follows the start of the half at 7 a.m. (The Hemingway 5K is also held in July, with a start time of 7:30 p.m. to take in the amazing sunset.)

In true festive Key West style, participants pick up their bibs at the expo held inside the Waterfront Brewery, and finish in walking distance to the famous Half Shell Raw Bar, where you can enjoy delicious seafood after the race.

The larger lesson is this: This winter, if you happen to live in a northern city, why not indulge your inner snowbird and plan to join a road race in a temperate clime of spectacular beauty?

Bermuda Marathon Weekend
Another favorite destination race—occurring during the same January 13-15 weekend—is the cluster of events known as Bermuda Marathon Weekend, featuring up to three days of races. If you have no work on Martin Luther King, Jr. Day on January 16, you just might consider trying all three, given the extra day to put your feet up. In any case, there’s something for everyone at this first-class destination race. The 2017 schedule is as follows:

On Friday (the 13th—tread carefully!) the Front Street Mile kicks things off at 7 p.m. Saturday morning features a 10K that also permits walking. Sunday is the main event, 26.2 miles of rolling course with scenes of clear waters, lush foliage and pastel buildings to distract and entertain you the entire time.

Less ambitious travelers can also choose the half-marathon on Sunday. But complete either the first two plus the half, or the first two plus the marathon, and consider yourself a bona fide Bermuda Triangle Challenger. At postcard sending  time, that’s something to write home about.

At, the race organizers proudly note that Bermuda is only a two-hour (or less) flight from most east coast cities and Toronto.

Gasparilla Distance Classic
For a third option, coming up on February 25-26, 2017, it’s back to Florida for the Gasparilla Distance Classic in Tampa, Florida ( This time there are four races over two days from which to choose: a 5K, 8K, 15K and a half-marathon. The race distances are staggered across the two days, with the 5K and 15K on Saturday and the 8K and half on Sunday.

As with the Bermuda Triangle Challenge, participants are eligible to run as many of these as they like. However you choose to experience the Distance Classic, you’ll be doing something good—the Gasparilla Distance Classic Association is a nonprofit “dedicated specifically to raising funds for charitable youth organizations and running programs in the Tampa Bay area,” according to their mission statement.

Since the first running back in 1978, the group reports that they have raised and donated some $4.4 million to the Boys & Girls Clubs of Tampa, Girls Inc. of Pinellas, The Friends of Tampa Parks & Recreation and youth running-related programs. It most likely does not hurt their cause that the half-marathon offers sweeping views of Tampa Bay along Bayshore Boulevard and as you cross the bridge out to Davis Islands.

Runner's World, May 14, 2015, "Bucket List: 9 Destination Half Marathons," by Kit Fox,

Key West Half Marathon & 5K,

Rails to Trails Conservancy, Dec. 2013, "Connecting the Keys: Florida Keys Overseas Heritage Trail," by Sher Jasperse,

Bermuda Marathon Weekend,

Gasparilla Distance Classic,

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