54 Upcoming Races Near Middleburg, VA - Matching: Trail Races

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Sat, Nov 142 races

Berryville Turkey Trot 5K & 1 Mile Kids Fun Run logo

Berryville Turkey Trot 5K & 1 Mile Kids Fun Run

Berryville, VA

5K
1 Mile
Trail
View details for race Berryville Turkey Trot 5K & 1 Mile Kids Fun Run
Fall for the Park 5.5K & Flannel Fest logo

Fall for the Park 5.5K & Flannel Fest

Manassas Park, VA

5K
Trail
View details for race Fall for the Park 5.5K & Flannel Fest
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Sun, Nov 152 races

Fall Backyard Burn Trail Run - Hemlock Overlook logo

Fall Backyard Burn Trail Run - Hemlock Overlook

Clifton, VA

Trail
View details for race Fall Backyard Burn Trail Run - Hemlock Overlook

2026 Chasing Zero 5.5k (and 22k) Turkey Trot

Hamilton, VA

Trail
View details for race 2026 Chasing Zero 5.5k (and 22k) Turkey Trot

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Sat, Nov 211 race

Herndon Turkey Trot 5K logo

Herndon Turkey Trot 5K

Herndon, VA

5K
Trail
View details for race Herndon Turkey Trot 5K

Sun, Nov 222 races

Maryland Turkey Trot 5k & 10k logo

Maryland Turkey Trot 5k & 10k

Potomac, MD

5K
10K
Trail
Fast
View details for race Maryland Turkey Trot 5k & 10k
Fall Backyard Burn Trail Run - Riverbend logo

Fall Backyard Burn Trail Run - Riverbend

Great Falls, VA

10 Miles
Trail
View details for race Fall Backyard Burn Trail Run - Riverbend

Wed, Nov 251 race

Winery at Bull Run Turkey Trot 5k & 10k logo

Winery at Bull Run Turkey Trot 5k & 10k

Centreville, VA

5K
10K
Trail
View details for race Winery at Bull Run Turkey Trot 5k & 10k

Thu, Nov 265 races

Blue Crab Turkey Trot 5k & 10k logo

Blue Crab Turkey Trot 5k & 10k

Silver Spring, MD

5K
10K
Trail
View details for race Blue Crab Turkey Trot 5k & 10k
Burke Lake Turkey Trot 5k & 10k logo

Burke Lake Turkey Trot 5k & 10k

Fairfax Station, VA

Trail
View details for race Burke Lake Turkey Trot 5k & 10k
South Run Turkey Trot 5k & 10k logo

South Run Turkey Trot 5k & 10k

Springfield, VA

5K
10K
Trail
View details for race South Run Turkey Trot 5k & 10k

2026 Annual AKT Turkey Trot 5K/10K

Alexandria, VA

5K
10K
Trail
View details for race 2026 Annual AKT Turkey Trot 5K/10K
United Way of the Eastern Panhandle Turkey Trot logo

United Way of the Eastern Panhandle Turkey Trot

Martinsburg, WV

5K
Trail
View details for race United Way of the Eastern Panhandle Turkey Trot

Fri, Nov 272 races

Black Friday 5k & 10k logo

Black Friday 5k & 10k

Herndon, VA

5K
10K
Trail
View details for race Black Friday 5k & 10k
Haraka Run and Walk Black Friday Fun Run logo

Haraka Run and Walk Black Friday Fun Run

Hyattsville, MD

Trail
Fast
View details for race Haraka Run and Walk Black Friday Fun Run

Sat, Nov 281 race

Ugly Sweater Dash 5k, 10k, & Half logo

Ugly Sweater Dash 5k, 10k, & Half

Fairfax Station, VA

Half
5K
10K
Trail
View details for race Ugly Sweater Dash 5k, 10k, & Half

Sat, Dec 51 race

Froggy Hollow 5 & 9 presented by Altra logo

Froggy Hollow 5 & 9 presented by Altra

Clarksburg, MD

Trail
View details for race Froggy Hollow 5 & 9 presented by Altra

Sun, Dec 62 races

Fall Backyard Burn Trail Run - Fountainhead logo

Fall Backyard Burn Trail Run - Fountainhead

Fairfax Station, VA

Trail
View details for race Fall Backyard Burn Trail Run - Fountainhead
OLD TOWN RUN CLUB JINGLE BELL 5K & KIDS 1 MILER RUN/WALK logo

OLD TOWN RUN CLUB JINGLE BELL 5K & KIDS 1 MILER...

Alexandria, VA

Trail
View details for race OLD TOWN RUN CLUB JINGLE BELL 5K & KIDS 1 MILER RUN/WALK

Sat, Dec 122 races

=PR= Races: Holiday Run Fest - Half Marathon, 4 Miler, & Challenge logo

=PR= Races: Holiday Run Fest - Half Marathon, 4...

Annandale, VA

Half
Trail
View details for race =PR= Races: Holiday Run Fest - Half Marathon, 4 Miler, & Challenge
Holiday 4 Miler logo

Holiday 4 Miler

Springfield, VA

Trail
View details for race Holiday 4 Miler

Sun, Dec 132 races

Fleet Feet Fredericksburg's Jolly Jog logo

Fleet Feet Fredericksburg's Jolly Jog

Fredericksburg, VA

5K
Trail
View details for race Fleet Feet Fredericksburg's Jolly Jog
Fleet Feet Woodbridge's Jolly Jog 2026 logo

Fleet Feet Woodbridge's Jolly Jog 2026

Lorton, VA

5K
Trail
View details for race Fleet Feet Woodbridge's Jolly Jog 2026

Sat, Dec 191 race

Candy Cane 5k & 10k logo

Candy Cane 5k & 10k

Alexandria, VA

5K
10K
Trail
View details for race Candy Cane 5k & 10k

Thu, Dec 241 race

Burke Lake Christmas Eve 5k & 10k logo

Burke Lake Christmas Eve 5k & 10k

Fairfax Station, VA

5K
10K
Trail
View details for race Burke Lake Christmas Eve 5k & 10k

Sat, Dec 261 race

Boxing Day 5k & 10k logo

Boxing Day 5k & 10k

Annandale, VA

5K
10K
Trail
View details for race Boxing Day 5k & 10k

Thu, Dec 311 race

Running Out of Time 5k & 12k logo

Running Out of Time 5k & 12k

Fairfax Station, VA

5K
Trail
View details for race Running Out of Time 5k & 12k

Sun, Jan 10, 20272 races

Run at the Boathouse 5k & 10k logo

Run at the Boathouse 5k & 10k

Alexandria, VA

5K
10K
Trail
View details for race Run at the Boathouse 5k & 10k
Patriotic Pursuit 5k, 10k & Half logo

Patriotic Pursuit 5k, 10k & Half

Williamsport, MD

Half
5K
10K
Trail
View details for race Patriotic Pursuit 5k, 10k & Half

Mon, Jan 18, 20271 race

MLK Day 5k & 10k logo

MLK Day 5k & 10k

Silver Spring, MD

5K
10K
Trail
View details for race MLK Day 5k & 10k

Sun, Jan 31, 20271 race

The Great Frosty Forest 5k/10k/Half/Marathon/50k logo

The Great Frosty Forest 5k/10k/Half/Marathon/50k

Dumfries, VA

Half
5K
Marathon
Trail
View details for race The Great Frosty Forest 5k/10k/Half/Marathon/50k

Sat, Feb 27, 20271 race

Belle Haven 5k & 10k logo

Belle Haven 5k & 10k

Belle Haven, VA

5K
10K
Trail
View details for race Belle Haven 5k & 10k

Sat, Mar 6, 20273 races

MCRRC Seneca Creek Greenway Trail Marathon & 50K logo

MCRRC Seneca Creek Greenway Trail Marathon & 50K

Gaithersburg, MD

Marathon
Ultra
Trail
View details for race MCRRC Seneca Creek Greenway Trail Marathon & 50K
Potomac River Views 5k & 10k logo

Potomac River Views 5k & 10k

Alexandria, VA

5K
10K
Trail
View details for race Potomac River Views 5k & 10k
Half Donkey (Half/10k/5k) logo

Half Donkey (Half/10k/5k)

Alexandria, VA

Half
10K
5K
Trail
Fast
View details for race Half Donkey (Half/10k/5k)

Sun, Mar 14, 20271 race

Tree of Life 10K, 5K & Pioneer 1 Mile Race logo

Tree of Life 10K, 5K & Pioneer 1 Mile Race

Fredericksburg, VA

10K
5K
1 Mile
Trail
View details for race Tree of Life 10K, 5K & Pioneer 1 Mile Race

Sat, Mar 27, 20271 race

Vietnam Veteran's 5k logo

Vietnam Veteran's 5k

Warrenton, VA

5K
Trail
View details for race Vietnam Veteran's 5k

Sat, Apr 10, 20271 race

Run for the Wounded 5k, 10k, & Half logo

Run for the Wounded 5k, 10k, & Half

Triangle, VA

Half
5K
10K
Trail
View details for race Run for the Wounded 5k, 10k, & Half

Sat, May 1, 20272 races

Healthy Strides 5K 10K logo

Healthy Strides 5K 10K

Fairfax Station, VA

5K
10K
Trail
View details for race Healthy Strides 5K 10K
Trail Demon 5k & 10k logo

Trail Demon 5k & 10k

Bluemont, VA

5K
10K
Trail
View details for race Trail Demon 5k & 10k

Sat, May 15, 20272 races

Dreams for Veterans 5k & 10k logo

Dreams for Veterans 5k & 10k

Silver Spring, MD

5K
10K
Trail
View details for race Dreams for Veterans 5k & 10k
SHENANDOAH SKY logo

SHENANDOAH SKY

Bentonville, VA

Trail
View details for race SHENANDOAH SKY

Sun, May 16, 20271 race

2027 Capitol Hill Classic 10K, 3K, and Fun Run logo

2027 Capitol Hill Classic 10K, 3K, and Fun Run

Washington, DC

10K
Trail
View details for race 2027 Capitol Hill Classic 10K, 3K, and Fun Run

Sat, May 29, 20272 races

Heroes’ Memorial 5k & 10k logo

Heroes’ Memorial 5k & 10k

Derwood, MD

5K
10K
Trail
View details for race Heroes’ Memorial 5k & 10k
Heppe Chiropractic 15K & 5K logo

Heppe Chiropractic 15K & 5K

Fredericksburg, VA

15K
5K
Trail
View details for race Heppe Chiropractic 15K & 5K

Sun, Jun 6, 20271 race

Sarcoma Shuffle 5k & 10k logo

Sarcoma Shuffle 5k & 10k

Silver Spring, MD

5K
10K
Trail
View details for race Sarcoma Shuffle 5k & 10k

Mon, Jul 5, 20271 race

Maryland Fireworks 5k & 10k logo

Maryland Fireworks 5k & 10k

Silver Spring, MD

5K
10K
Trail
View details for race Maryland Fireworks 5k & 10k

Sun, Jul 18, 20271 race

Summer Dash 5k & 10k logo

Summer Dash 5k & 10k

Clarksburg, MD

5K
10K
Trail
View details for race Summer Dash 5k & 10k

Sun, Aug 8, 20271 race

Rock the Heat 5k & 10k logo

Rock the Heat 5k & 10k

Derwood, MD

5K
10K
Trail
View details for race Rock the Heat 5k & 10k

Sat, Aug 14, 20271 race

Ridge Reaper 5k & 10k logo

Ridge Reaper 5k & 10k

Clifton, VA

5K
10K
Trail
View details for race Ridge Reaper 5k & 10k
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