JFK 50 Mile

Event Overview

Course & Terrain

Point-to-point from downtown Boonsboro to Springfield Middle School in Williamsport. The first 5.5 miles climb 1,172 ft, joining the Appalachian Trail at mile 2.5. The course stays on the Appalachian Trail to mile 15.5, apart from two miles of paved road between miles 3.5 and 5.5, then drops more than 1,000 ft down the Weverton Cliffs switchbacks to the C&O Canal towpath. It follows the towpath for 26.3 flat miles to Dam #4 (mile 41.8) and finishes with 8.4 miles of gently rolling paved roads.

Key course features to know before comparing this race:

• Appalachian Trail along South Mountain, past Gathland State Park
• Weverton Cliffs switchbacks down to the Potomac River
• C&O Canal towpath past Harpers Ferry, the Antietam Aqueduct and Shepherdstown
• Off the towpath at Dam #4 and through Downsville to Williamsport
• Finish at Springfield Middle School, the finish line since 1980

The race has three distinct parts: about 13 miles of rocky, technical Appalachian Trail single-track, 26.3 miles of flat dirt and gravel towpath closed to vehicles, and 8.4 miles of paved country roads. The start in Boonsboro is at 570 ft and the finish in Williamsport at 452 ft.

The race is held on the Saturday before Thanksgiving in western Maryland. In 2025, iRunFar reported overnight rain that cleared before the start, leaving a damp course and plenty of fog.

Entry & Logistics

Why This Race Matters

The JFK 50 Mile is America's oldest ultramarathon. It was first held on March 30, 1963, as a Cumberland Valley Athletic Club event, one of many 50-mile challenges held across the country after President Kennedy asked military officers to meet Theodore Roosevelt's standard of 50 miles on foot in 20 hours. Four people finished the first race in 13:10, including founder William "Buzz" Sawyer. Nearly all the other Kennedy challenges stopped after his assassination. This one became the JFK 50 Mile Memorial in 1964 and has been held every year since, in November since 1975. Sawyer directed the first 30 editions, and Mike Spinnler, the 1982 and 1983 winner, has directed it since 1993. The race is open to everyone, but its top award, the Kennedy Cup, goes to the best military team. The 2026 race is the 64th edition.

Historical benchmark notes in the directory record (verify current records with the linked official sources):

• Men: David Sinclair, 5:08:27, 2024. He broke Hayden Hawks's 5:18:40 from 2020.
• Women: Rachel Drake, 5:57:33, 2024, the only women's time under six hours. She broke Sarah Biehl's 6:05:42 from 2022.
• Second-fastest men's time: Hans Troyer, 5:10:25, 2025.
• Masters records (40 and over): Howard Nippert, 5:51:28, 2005, and Caitriona Jennings, 6:28:53, 2022.
• Most wins: James "Big E" Ebberts, five; Donna Aycoth and Carolyn Showalter, six each. Jim Walmsley won three in a row from 2014 to 2016.
• Most finishes: Kimball Byron, 49; Carolyn Showalter, 38 through 2025.
• Military team record: U.S. Air Force, 34:46:45 for five runners, 2012.

Preparing for a Race Like JFK 50 Mile

The fixed-distance race guide covers the format as a whole. These guides go deeper:

• Walking strategy for ultramarathons: When and how to walk by terrain, effort and cutoffs.
• Crew and aid-station strategy: Crew tables, aid stops, drop bags and runner preferences.
• Hydration and sodium for ultramarathons: Fluid, sodium, thirst, sweat rate and hyponatremia risk.
• Tapering for ultramarathons: Plan the taper and race week around your own recovery.

Best Fit

• Runners stepping up to a first 50-miler with a 13-hour limit and heavy aid
• Fast runners chasing a quick 50-mile time on the flat towpath
• Military teams competing for the Kennedy Cup

Planning Notes

• The directory marks this as having comparatively simpler logistics. That editorial label is not a safety rating; verify cutoffs, terrain, support, crew access, and withdrawal procedures.
• The first cutoff is mile 2.5 by 7:15 AM, 45 minutes after the start, on an uphill road
• Rocky Appalachian Trail single-track and the steep Weverton Cliffs switchbacks
• Headphones and other personal listening devices lead to disqualification
• No pacers and no crew on the last 8.4 miles
• No race-morning packet pick-up

Event FAQs

Related Preparation

• Compare this race in the full 2026 calendar
• Open the Fixed-Distance format guide
• Compare all race formats
• Use the timed-race pace calculator
• Plan checkpoint arrivals and cutoff buffers
• Build a crew and drop-bag plan
• Build a race-specific gear checklist