Winchester · United States

Half Marathon races near Winchester

9 races in 2026 next one in 2 days

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Race calendar

Upcoming Half Marathon races near Winchester

This week 1

Run · road · Half Marathon

Eagle 5K, 10K, & 13.1M at Bel Air, MD (27)

Bel Air · 73 km away

AUG 3

Run · road · Half Marathon

Ninja 5K, 10K, & 13.1M at Bel Air, MD (31)

Bel Air · 73 km away

Run · road · Half Marathon

Third Winchester Battlefield 5k, 10k, & Half

Run · road · Half Marathon

Howard's Half Marathon/5K Run Festival

Cumberland · 73 km away

SEP 5

Run · road · Half Marathon

Medal Madness 5K, 10K, & 13.1M at Bel Air, MD (36)

Bel Air · 73 km away

+4 more Half Marathon racesShow fewer ↓

Run · road · Half Marathon

Lock 2 Lock Marathon/Half Marathon/10k

Williamsport · 55 km away

Run · road · Half Marathon

Shenandoah River 5k, 10k, & Half

Bentonville · 42 km away

Run · road · Half Marathon

Run On The Rocks

Point of Rocks · 56 km away

Run · road · Half Marathon

Run On The Rocks • 10M / Half / 20M

Point Of Rocks · 54 km away

Winchester · 80 km

9 races mapped View on map →

Recurring Half Marathon races near Winchester

Races that repeat — weekly, monthly or yearly

Haunted 5K, 10K & 13.1M at Bel Air, MD (40)

The Haunted 5K, 10K & 13.1M in Bel Air, Maryland, starts at 8:00 AM and offers 5K, 10K, and half marathon distances. All participants must register in advance via RunSignup; no race-day registration is available. Packet pickup occurs on race morning only, from 30 minutes before the start until 10 minutes prior. The courses consist of repeating out-and-back segments. The 5K course is a 1.56-mile out-and-back completed twice. The 10K uses the same segment four times, and the half marathon covers a 2.18-mile out-and-back segment six times. With a 3-hour, 30-minute time limit, the half marathon configuration is suited for runners who do not mind crossing the same section multiple times.

Freedom's Run ties its races to places where Civil War history is part of the ground underfoot: Harpers Ferry, Antietam, and the surrounding region. The series includes a May Harpers Ferry Half & 5K and an October Freedom's Run event, with distances ranging from a full marathon and half marathon to a 10K, 5K, and Kids Fun Run. The Harpers Ferry races run inside Harpers Ferry National Park, while the longer Freedom's Run routes connect runners with historic sites in and around the area. One runner remembered entering Antietam in cold rain, with mist rising from wet earth and the field going quiet as the group ran together. The series also links to Two Rivers Treads, a local running store with a foot-first approach to shoes and gait, and it raises money for a community grant fund supporting local health and community projects.

Buzz Sawyer Western Maryland Marathon/Half Marathon/10k

The Buzz Sawyer Western Maryland Marathon/Half Marathon/10k begins and ends in Hancock, Maryland. All three races take place on the Western Maryland Rail Trail. This October event offers marathon, half marathon, and 10k distances. The marathon and half marathon courses are USATF certified. The marathon is also a Boston Marathon qualifier, attracting runners aiming for a qualifying time and locals seeking a trail race. The course is entirely on the WMRT, a rail trail passing through a town linked to trail travel and C&O Canal history. This is the race's 11th edition, now named for Buzz Sawyer, a Washington County distance runner, coach, race director, and founder of the JFK50 Miler. Katie and Adam Lowe of 2Lowe Run Company direct the event, having taken over from Frank and Mike of Altis Endurance, with the goal of upholding the race's local traditions.

Schaeffer Half Marathon, 10K, 5K Trail Run

The Schaeffer series is a trail-running event by EX2 Adventures held in Maryland and Virginia. It offers three race distances: a half marathon, a 10K, and a 5K trail run. This event is designed for runners seeking a trail experience over a road race. The format provides participants with a choice between a longer trail effort, a middle-distance run, and a shorter option. EX2 Adventures also organizes adventure racing and triathlon events, placing the series within the region's wider outdoor endurance calendar.

Holiday 5K, 10K, & 13.1M at Bel Air, MD (49)

View all recurring races near Winchester →

Looking for something else near Winchester?

5K running Winchester → 71 10K running Winchester → 38 Marathon running Winchester → 3

Other races in the next 90 days

All sports & distances →

JUL 1157 km away cycling

San Mar's The Great Bicycle Tour - TGBT XXXIX

road155.3 km296.9 km

JUL 1146 km away multisport

Seven Bends Adventure Race

trail3.2 km8.1 km11.3 km

JUL 1268 km away triathlon

Rocky Gap Off-Road Triathlon, Duathlon, Aqua Bike, and Relay

17.3 km22.8 km31.9 km

JUL 1246 km away duathlon

Seven Bends Aqua Blaze

3.2 km8.1 km11.3 km

JUL 1766 km away cycling

Women+ TakeOver at Bryce

JUL 1835 km away triathlon

Martinsburg Sprint & Super Sprint

JUL 2570 km away cycling

Dirty Kitten Gravel Fest!

gravel32.2 km64.4 km96.5 km

JUL 2661 km away triathlon

LoCo Sprint Tri

About Half Marathon races in Winchester

Winchester Training Notes

Winchester hosts 14 Half Marathon races in 2026 within 80 km of the city centre — upcoming dates, recurring series, and other races nearby, all in one place.

Locals run Winchester through Old Town, Rose Hill Park, and Sherando Park. The 25-mile loop trail works when the day calls for easy Z2 or quick intervals. Sherando Park mixes paved paths and wooded trails, so trail legs get work without leaving the local orbit. Shenandoah Valley Runners keeps the scene serious with group runs and races across Winchester, Frederick County, and West Virginia. Runners' Retreat hosts weekly runs through town. Old Town Winchester gets the Loudoun Street Mile. Third Winchester Battlefield 5k, 10k, & Half and Apple Blossom 10K anchor the calendar.

Winchester Wheelmen Bicycle Club carries the riding scene, and the club has been the cyclists' voice in the northern Shenandoah Valley since 1973. Locals use its Frederick County rides for base miles, classes, and outreach. The route covers 7 km with 1,061 m of ascent and 1,007 m of descent. The next segment is 4 km adding 100 m of ascent and 80 m of descent. Sherando Park bike trails handle mixed-terrain days. The 6th Annual CCAP Benefit Bike Tour 2026 works as the anchor ride.

May, June, July, August, and September give Winchester its best training block. Summer brings the SPEAR TRAIL SERIES onto Sherando Park bike trails, while Heatwave Hustle 5k & 10k in June and Glow All Out 5K Glow Run in July keep runners honest. Locals treat the warm months as race season, gran fondo prep, and steady base miles. Winter changes the rhythm. SVR sponsors the SVR Winter Series, so runners still have structure when the easy miles get colder. Cyclists lean on the Winchester Wheelmen ride network and the familiar Frederick County routes when the event calendar quiets down.