Winchester · United States

5K races near Winchester

38 races in 2026 next one in 2 days

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Race calendar

Upcoming 5K races near Winchester

This week 6

Run · road · 5K

IMDC Freedom Firecracker 5K and Sparkler 1-Mile

Manassas · 73 km away

Run · road · 5K

Greg Shank Memorial 5K Run/Walk

Williamsport · 55 km away

Run · road · 5K

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

Bel Air · 73 km away

Run · road · 5K

Fourth of July 5K Fun Run

Great Falls · 79 km away

Run · road · 5K

Red, White & Run 5k

Aldie · 58 km away

+33 more 5K racesShow fewer ↓

Run · road · 5K

FSRC Independence 5000

Frederick · 72 km away

JUL 6

Run · road · 5K

Moonlight 5K and Twilight Kids Run presented by Brooks

Bel Air · 73 km away

Run · road · 5K

Great Country Farms 5k & 10k

Bluemont · 31 km away

Run · road · 5K

Glow All Out 5K Glow Run

Run · trail · 5K

Summer Dash 5k & 10k

Clarksburg · 76 km away

Run · trail · 5K

868 Estate Vineyards 5k & 10k

Purcellville · 39 km away

Run · road · 5K

=PR= Races: PR Bash 5K

Ashburn · 63 km away

AUG 12

Run · road · 5K

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

Bel Air · 73 km away

Run · road · 5K

Frederick Women's Distance Festival

Frederick · 68 km away

Run · road · 5K

Third Winchester Battlefield 5k, 10k, & Half

Run · trail · 5K

Summer Sprint 5k & 10k

Purcellville · 37 km away

Run · road · 5K

Jack Roberts Memorial 5K

Hagerstown · 64 km away

Run · road · 5K

Catch-A-Pig 5K & 1K Bacon Stroll

Bel Air · 73 km away

Run · road · 5K

Purcellville · 37 km away

Run · road · 5K

Leopold’s Preserve 5k & 10k

Broad Run · 61 km away

Run · road · 5K

Dulles 5K/10K on the Runway

Chantilly · 69 km away

Run · road · 5K

The Inferno 5k & 10k

Bluemont · 30 km away

Run · road · 5K

Howard's Half Marathon/5K Run Festival

Cumberland · 73 km away

Run · road · 5K

Sweet Run 5k & 10k

Hillsboro · 38 km away

SEP 14

Run · road · 5K

Dog Days of Summer 5k & 10k

Warrenton · 60 km away

Run · road · 5K

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

Bel Air · 73 km away

Run · road · 5K

Footprints of Hope 5K Run/Walk

Haymarket · 59 km away

Run · road · 5K

Othello Park Labor Day 1K/5k

Knoxville · 46 km away

Run · road · 5K

Montgomery County Interfaith 5K

Boyds · 74 km away

Run · road · 5K

The Cinnamon Bun Fun Run and 5K

Smithsburg · 73 km away

Run · road · 5K

Tails on Trails 5K Run/Walk

Berkeley Springs · 38 km away

Run · road · 5K

Williamsport · 55 km away

Run · road · 5K

Shenandoah River 5k, 10k, & Half

Bentonville · 42 km away

Run · road · 5K

MCRRC Country Road Run

Dickerson · 64 km away

Run · road · 5K

Color Splash 1K & 5K Run/Walk 2026

Hagerstown · 64 km away

Run · road · 5K

Eagle Nation 5k

Berryville · 14 km away

Run · road · 5K

River's Edge Endurance Challenge

Brunswick · 50 km away

Run · road · 5K

Lovettsville 5k & 10k

Lovettsville · 46 km away

Winchester · 80 km

38 races mapped View on map →

Recurring 5K 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.

Fall Harvest 5k

The Fall Harvest 5K begins at 9:00 a.m. starting from BB&T Bank. Morning registration and packet pickup are at the Borough Building on Filbert Street. This is a 3.1-mile road race on a flat, fast, wheel-measured course. The plan is straightforward: arrive early, attach your bib, and complete a quick local 5K. Awards are presented to the top three men and women in each age group, with divisions from under 10 to 70+. The fastest overall male and female runners receive trophies. The current course records are 16:56.80 for men and 17:20.65 for women. A $200 prize is offered for the first man and first woman to break the record in the new 70+ age group.

Friends of Reston Fall 5K

The Tie Dye Run takes place on a fall morning in Hagerstown, Maryland, starting at 17805 Oak Ridge Drive. Participants can choose from three distances: a 5K run/walk, a 10K run/walk, and a Family Fun Walk/Run. This setup accommodates both competitive runners aiming for a personal best and families seeking a shared activity. The family event begins earlier, with the 5K and 10K starting later in the morning after participants have checked in. The event is in its third year and benefits Compassion International, with all proceeds directed to the charity. Awards are presented to the top male and female finishers in the 5K and 10K, as well as to winners in various age groups, from youth categories up to 70 and older. Registration fees vary based on the chosen distance; the 10K is the most expensive, the family event is the least costly, and prices increase after the early registration period closes.

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.

Run Like Michael

Run Like Michael centers on Michael’s 5K Run For Life, a July race connected to Michael’s Run for Life Festival in Peoria. Packet pickup is handled at RC Outfitters on SW Water Street before race day, and on-site registration is available at the festival. The run was created because Michael loved running, and it supports the foundation’s fight against signet ring colon cancer. The event’s message is direct: a large group of people can take on hard problems together. The race gathers runners and supporters around that cause, rather than around a complicated course or elite field.

New Market STRONG Run/Walk and Festival

The New Market STRONG Run/Walk and Festival is an annual 5K in New Market, Maryland. It honors Karen Durbin, the town clerk who served the community for over 14 years before passing away after a prolonged battle with breast cancer. This 3.1-mile event accommodates both runners and walkers, with timing provided by Racine MultiSports. Families, walkers, and leashed dogs are welcome. The course follows New Market’s historic streets and adjacent neighborhoods, keeping the race centered on the town it benefits. Proceeds are directed to the Hurwitz Breast Cancer Fund, supporting the Frederick Health Hospital Cancer Center. Following the race, the event transitions into a local festival featuring live music, vendors, food and beverage trucks, family activities, and a cornhole competition.

The Run for MWS 5K is a regional race for Mowat-Wilson Syndrome held in Monocacy Village Park in Frederick, Maryland. The event offers a 5K run/walk and a shorter Fun Run, both starting at 10am, catering to runners, walkers, families, and supporters, not exclusively competitive racers. The course is set within the park, presenting a local, park-based charity race with two distance options. Every registrant receives a Run for MWS: Mid-Atlantic Regional race t-shirt, and participants are entered into prize drawings. Non-runners can participate via a support/spectator option which also includes a shirt.

Boulder Dash at Pinesburg Quarry

Boulder Dash uses the roads and packed gravel surrounding Pinesburg Quarry in Williamsport, Maryland, as the quarry itself is closed for race-day safety. The annual event provides three options: a challenging 5 Mile Challenge, a moderate Family Friendly 5K, and an accessible 1 Mile Fun Run. The 1-mile race begins at 9:30 a.m., followed by the 5K and 5-mile races at 10:00 a.m. It accommodates a broad range of participants, from novices and families to those seeking a more strenuous quarry race. The 5 Mile Challenge is the notable course, descending into both the main and old quarry sections, featuring hills, packed gravel, uneven terrain, and some rocky parts. The 5K remains outside the quarry pits on gently rolling roads and gravel, while the 1-mile route is flat and suitable for children or less experienced runners. Registration covers a shirt, custom bib, finisher medal, complimentary photos, and post-race awards. Chip timing and live results are managed by Racine Timing. Awards are presented to the top overall male and female finishers and age-group winners in the 5K and 5-mile races, with 5-mile age groups ranging from 15-and-under up to 80.

Ghostly Grapes 5k & 10k at Two Twisted Posts

The Ghostly Grapes 5k & 10k is a fall trail run and walk held at Two Twisted Posts Winery & Tavern in Purcellville, Virginia. Participants select either a 5K or 10K distance, with both courses utilizing the winery's property and nearby trails by Short Hill Mountain. BISHOP'S EVENTS organizes the run, which accommodates both walkers and runners in a relaxed atmosphere. The start and finish lines are located at the winery on Harpers Ferry Road, leading participants back to post-run food, beer, music, and wine. A complimentary glass of wine is included after the run. The Ghostly Grapes theme incorporates costumes, awards, and race shirts. The event also supports a charity, and early registration provides a reduced fee.

Run the Vineyards - Rocklands Farm 5K

Run the Vineyards - Rocklands Farm 5K is a 5-kilometer race at Rocklands Farm Winery in Poolesville, Maryland, with the start on the winery property. It is a cross-country style run rather than a road 5K, using hard-packed dirt, gravel, and grass trails through vineyard and farm terrain. The race uses chip timing with instant results, and the marked course includes hydration stations and volunteer support. Walkers and children can join, though walkers must register and start behind the runners, and everyone has a one-hour course limit. The event leans into the winery setting after the finish. Participants over 21 get a complimentary drink ticket, with wine tasting and wine sales available on site, plus live music, a food truck, and indoor and outdoor seating. Awards go to the top overall finishers and to age-group winners, three deep for male and female categories, starting with Under 14 and then moving through standard age bands. Registration also includes a custom tech shirt, a souvenir wine glass, free race photos, and free parking, with optional upgrades for long sleeves and finisher medals.

Halloween Horror 5k & 10k

View all recurring races near Winchester →

Looking for something else near Winchester?

10K running Winchester → 38 Half Marathon running Winchester → 14 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 5K races in Winchester

Winchester Training Notes

Winchester hosts 71 5K 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.