48 Upcoming Races Near Middletown, MD - Matching: Trail Races

Most popular races in Maryland →

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

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

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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

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

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
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

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 282 races

NCR Marathon & Half Marathon logo

NCR Marathon & Half Marathon

Sparks Glencoe, MD

Marathon
Half
Trail
Fast
BQ
View details for race NCR Marathon & Half Marathon
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

Holiday 4 Miler logo

Holiday 4 Miler

Springfield, VA

Trail
View details for race Holiday 4 Miler
=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

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

Little Patuxent River Half Marathon, 10K, & 5K logo

Little Patuxent River Half Marathon, 10K, & 5K

Columbia, MD

5K
10K
1 Mile
Trail
View details for race Little Patuxent River Half Marathon, 10K, & 5K

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)

Sat, Apr 10, 20271 race

Charity Cooperative Arlington Area 5k logo

Charity Cooperative Arlington Area 5k

Arlington, VA

5K
Trail
View details for race Charity Cooperative Arlington Area 5k

Sun, Apr 11, 20271 race

3rd Annual Bruce Hollabaugh Memorial 5K & Fun Run logo

3rd Annual Bruce Hollabaugh Memorial 5K & Fun Run

Biglerville, PA

5K
1 Mile
Trail
View details for race 3rd Annual Bruce Hollabaugh Memorial 5K & Fun Run

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, 20271 race

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

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, 20271 race

Heroes’ Memorial 5k & 10k logo

Heroes’ Memorial 5k & 10k

Derwood, MD

5K
10K
Trail
View details for race Heroes’ Memorial 5k & 10k

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

Sat, Jul 17, 20271 race

Great Appalachian Valley Race: Half Marathon, 10K and 5K logo

Great Appalachian Valley Race: Half Marathon, 1...

Shippensburg, PA

Half
10K
5K
Trail
Fast
View details for race Great Appalachian Valley Race: Half Marathon, 10K and 5K

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

Sat, Jul 24, 20271 race

Tommy Laudani Delone Dash 5K/3K Trail Run logo

Tommy Laudani Delone Dash 5K/3K Trail Run

Hanover, PA

5K
Trail
View details for race Tommy Laudani Delone Dash 5K/3K Trail Run

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

Sun, Aug 22, 20271 race

Leopold’s Preserve 5k & 10k logo

Leopold’s Preserve 5k & 10k

Broad Run, VA

5K
10K
Trail
View details for race Leopold’s Preserve 5k & 10k

Sat, Sep 18, 20271 race

The Final Countdown - Tribute logo

The Final Countdown - Tribute

Martinsburg, WV

Trail
Fast
View details for race The Final Countdown - Tribute

Sun, Oct 31, 20271 race

Halloween Horror 5k & 10k logo

Halloween Horror 5k & 10k

Gainesville, VA

5K
10K
Trail
View details for race Halloween Horror 5k & 10k