178 Upcoming Races Near Chestertown, MD

Sat, Dec 55 races

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

Bel Air, MD

10K

Half

Fast

View details for race Holiday 5K, 10K, & 13.1M at Bel Air, MD (49)

DeCesaris Prout Cancer Foundation - Jingle Bell...

Annapolis, MD

View details for race DeCesaris Prout Cancer Foundation - Jingle Bell 5K/3K

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$5 5K Series: 2026 Reindeer Run

Baltimore, MD

View details for race $5 5K Series: 2026 Reindeer Run

Wright Stuff 8K

College Park, MD

View details for race Wright Stuff 8K

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Jolly Jingle

Wilmington, DE

View details for race Jolly Jingle

Sun, Dec 66 races

Stocking Suffer 8-Hour Endurance Run

Stevensville, MD

Trail

View details for race Stocking Suffer 8-Hour Endurance Run

Hot Chocolate Run

Bel Air, MD

View details for race Hot Chocolate Run

Holiday Hustle

Parkville, MD

View details for race Holiday Hustle

9th Annual Homewood Holiday 5k

Baltimore, MD

View details for race 9th Annual Homewood Holiday 5k

12th Annual Angel Park Jingle All The Way 5k & ...

Perry Hall, MD

1 Mile

View details for race 12th Annual Angel Park Jingle All The Way 5k & 1 Mile Family Fun Run

Freedom Hills Therapeutic Riding Reindeer Run 5K

Port Deposit, MD

View details for race Freedom Hills Therapeutic Riding Reindeer Run 5K

Sat, Dec 123 races

The Santa Cause 5K

Newark, DE

View details for race The Santa Cause 5K

Celtic Solstice Five-Miler

Baltimore, MD

View details for race Celtic Solstice Five-Miler

Jingle Hills Run

Bel Air, MD

View details for race Jingle Hills Run

Sun, Dec 133 races

Holiday Hustle 5K and Jingle Jog Kids Run

Bel Air, MD

View details for race Holiday Hustle 5K and Jingle Jog Kids Run

CCD’s Holiday Race for Recovery 5K

New Castle, DE

View details for race CCD’s Holiday Race for Recovery 5K

Anniversary Run 15K

Annapolis, MD

15K

View details for race Anniversary Run 15K

Fri, Dec 181 race

Holiday Lights Run

Bel Air, MD

View details for race Holiday Lights Run

Sat, Dec 192 races

Reindeer Run 5k

Aberdeen, MD

1 Mile

Fast

View details for race Reindeer Run 5k

Naptown Half Marathon & 10K/5K

Annapolis, MD

Half

10K

Trail

View details for race Naptown Half Marathon & 10K/5K

Sun, Dec 201 race

Egg Nog Mile

Havre de Grace, MD

1 Mile

View details for race Egg Nog Mile

Sun, Dec 274 races

SocaRobics® Old Year’s Day Skeleton Crew Fun Run

Owings Mills, MD

View details for race SocaRobics® Old Year’s Day Skeleton Crew Fun Run

Autumn Arch Winter Warmer 5K

Newark, DE

Fast

View details for race Autumn Arch Winter Warmer 5K

North by North 5k

Bel Air, MD

Trail

View details for race North by North 5k

Terrapin Trot 5k & 10k

Stevensville, MD

10K

View details for race Terrapin Trot 5k & 10k

Thu, Dec 311 race

New Year's Eve Gala

Bel Air, MD

View details for race New Year's Eve Gala

Fri, Jan 1, 20274 races

Hoppy New Year 5K

Newark, DE

View details for race Hoppy New Year 5K

Resolution Run 5K

Perryville, MD

1 Mile

View details for race Resolution Run 5K

Resolution Run

Baltimore, MD

1 Mile

15K

View details for race Resolution Run

18th Annual Chesapeake City New Years Day 5k

Chesapeake City, MD

View details for race 18th Annual Chesapeake City New Years Day 5k

Sat, Jan 2, 20271 race

New Year 5K, 10K, & 13.1M at Bel Air, MD (01)

Bel Air, MD

10K

Half

Fast

View details for race New Year 5K, 10K, & 13.1M at Bel Air, MD (01)

Sun, Jan 3, 20271 race

Fun Run and Championship Series Award Ceremony

Newark, DE

View details for race Fun Run and Championship Series Award Ceremony

Sat, Jan 9, 20272 races

Chill Chase 5k & 10k

Bladensburg, MD

10K

View details for race Chill Chase 5k & 10k

44th Icicle Ten Miler & Snowflake 5k

Wilmington, DE

View details for race 44th Icicle Ten Miler & Snowflake 5k

Sun, Jan 10, 20271 race

Tyler Brown's "I Hate to Run" Memorial 5K

Wilmington, DE

View details for race Tyler Brown's "I Hate to Run" Memorial 5K

Sat, Jan 16, 20271 race

PHUNT 25K/50K TRAIL RACE

Elkton, MD

Trail

View details for race PHUNT 25K/50K TRAIL RACE

Sat, Jan 23, 20272 races

Cocoa & Cupcakes 5K

Newark, DE

View details for race Cocoa & Cupcakes 5K

Terrapin Cult Classic 5k & 10k

Stevensville, MD

10K

View details for race Terrapin Cult Classic 5k & 10k

Tue, Jan 26, 20271 race

Test Race/Bren

Bel Air, MD

10K

Fast

View details for race Test Race/Bren

Sun, Jan 31, 20271 race

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

Columbia, MD

10K

1 Mile

Trail

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

Sat, Feb 6, 20271 race

Pirate 5K, 10K, & 13.1M at Bel Air, MD (06)

Bel Air, MD

10K

Half

Fast

View details for race Pirate 5K, 10K, & 13.1M at Bel Air, MD (06)

Sat, Feb 13, 20273 races

Cupid's Chase 5K Annapolis

Annapolis, MD

View details for race Cupid's Chase 5K Annapolis

Valentine 5K by Blue Cheetah Sports Timing

Perryville, MD

1 Mile

Fast

View details for race Valentine 5K by Blue Cheetah Sports Timing

Cupid's Chase 5K Baltimore

Baltimore, MD

View details for race Cupid's Chase 5K Baltimore

Sun, Feb 14, 20271 race

Touchdown 5K

Newark, DE

View details for race Touchdown 5K

Sun, Feb 21, 20271 race

The 2027 Maryland Indoor 5k and Family Fun Run ...

Hanover, MD

1 Mile

View details for race The 2027 Maryland Indoor 5k and Family Fun Run at Arundel Mills Mall!

Sat, Feb 27, 20271 race

Rosaryville Ramble 5k, 10k & Half

Upper Marlboro, MD

Half

10K

View details for race Rosaryville Ramble 5k, 10k & Half

Sat, Mar 6, 20271 race

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

Bel Air, MD

10K

Half

Fast

View details for race Medal Madness 5K, 10K, & 13.1M at Bel Air, MD (10)

Sun, Mar 7, 20272 races

B&A Trail Marathon and Half Marathon

Severna Park, MD

Marathon

Half

Trail

Fast

View details for race B&A Trail Marathon and Half Marathon

The Holly’s Hustle 5k Run/Walk

Smyrna, DE

View details for race The Holly’s Hustle 5k Run/Walk

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