Find Cycling Events in the State of Maryland.
January 2025-
Jan 6 - Mar 13, Kelley Acres Speed Shop 2025 10 Week Winter Performance Training Program
Middletown, MD
Recreational
Kelley Acres Speed Shop 2025 10 Week Winter Performance Training Program
Jan 12, 2025, Garrett County Fat Bike - Lions Club
McHenry, MD
4 laps
February 2025-
Feb 8, Otterhaus Coaching Trade Zone Training Series #1
Upper Marlboro, MD
75 minutes, 60 minutes, 45 minutes, 30 minutes
USA Cycling
Road Race MABRA
Feb 9, Garrett County Fat Bike - Herrington Manor
Oakland, MD
3 laps
Fat Bike Mountain Bike
Garrett County Fat Bike - Herrington Manor
March 2025-
Jan 6 - Mar 9, Dirty Kitten Winter Training Series 5.0
Frederick, MD
Virtual
Dirty Kitten Winter Training Series 5.0
Mar 22, Artemis Racing 25th Anniversary Celebration - 25 Years of Purple Reign
Mitchellville, MD
Special Event Road Race
April 2025-
Apr 12, Spring Fever MTB @ Fair Hill - XC/Endurance Race (Mid-Atlantic Super Series)
Elkton, MD
7 miles, 21 miles, 14 miles, 4 + hours
Mountain Bike Mid Atlantic Super Series
Apr 26, Poolesville Road Race -- 29th Edition
Poolesville, MD
63 miles, 53 miles, 42 miles, 32 miles
USA Cycling
Road Race MABRA
Poolesville Road Race -- 29th Edition
May 2025-
Jan 6 - Mar 13, Kelley Acres Speed Shop 2025 10 Week Winter Performance Training Program
Middletown, MD
Recreational
Kelley Acres Speed Shop 2025 10 Week Winter Performance Training Program
Jan 12, 2025, Garrett County Fat Bike - Lions Club
McHenry, MD
4 laps
February 2025-
Feb 8, Otterhaus Coaching Trade Zone Training Series #1
Upper Marlboro, MD
75 minutes, 60 minutes, 45 minutes, 30 minutes
USA Cycling
Road Race MABRA
Feb 9, Garrett County Fat Bike - Herrington Manor
Oakland, MD
3 laps
Fat Bike Mountain Bike
Garrett County Fat Bike - Herrington Manor
March 2025-
Jan 6 - Mar 9, Dirty Kitten Winter Training Series 5.0
Frederick, MD
Virtual
Dirty Kitten Winter Training Series 5.0
Mar 22, Artemis Racing 25th Anniversary Celebration - 25 Years of Purple Reign
Mitchellville, MD
Special Event Road Race
April 2025-
Apr 12, Spring Fever MTB @ Fair Hill - XC/Endurance Race (Mid-Atlantic Super Series)
Elkton, MD
7 miles, 21 miles, 14 miles, 4 + hours
Mountain Bike Mid Atlantic Super Series
Apr 26, Poolesville Road Race -- 29th Edition
Poolesville, MD
63 miles, 53 miles, 42 miles, 32 miles
USA Cycling
Road Race MABRA
Poolesville Road Race -- 29th Edition
May 2025-
Saturday, May 10 Tri-County Ice Cream Classic
Cycling event website: Tri-County Ice Cream Classic
Cycling event is for/about: Supporting Wounded Warriors & The Harriett Tubman Museum
Cycling event categories: Tri-County ice cream classic 2025 Chesapeake Cycling Club's Spring Road Cycling Event
Cycling event location- Talbot County Community Center 10028 Ocean Gateway Easton, MD 21601
Additional comments about event:
Check In Starts
102.2 Mile Course 7:00AM with 6:30am option
64.5 Mile Course 7:30AM
38.6 Mile Course 8:00AM
Register Here!
Free Stuff: Camelbak water bike bottle to each participant!
Plus free one-way passage on the Oxford-Bellevue Ferry!
Complimentary finish line food and beer:
Tacos by Papuseria Kent Island Food Truck.
Scottish Highland Creamery Ice Cream pit stop.
Live music by New Legacy Blues Band.
NEW FOR 2025!
"The Scoop" Swap & Sell!
Buy, sell, swap, trade . . . It's a classic swap meet!
Admission is FREE to all registered participants.
Those planning to offer items for sale MUST reserve tables in advance. Tables are FREE!
May 10, 2025 from 11:30AM - 3:00PM, at the Talbot County Community Center.
Please email Eric Griffioen HERE to reserve in advance.
Supporting Wounded Warriors & The Harriett Tubman Museum
Rest Stops for 102.2-Mile Course Register Here!
Rest Stop #1 from 7:30AM to 11:00AM at Mile 22, Adkins Arboretum , 12610 Eveland RD, Ridgely MD.
Rest Stop #2 from 8:30:AM to 12:00PM at Mile 40, Talbot Mentors 108 Maryland Avenue, Easton MD.
Rest Stop #3 from 10:30AM to 1:00PM at Mile 63, 3748 Main Street, Trappe, MD.
Rest stop #4 from 11:00AM to 1:30PM at Mile 75, Oxford-Bellevue Ferry Landing, Ferry Crossing Slip road, Oxford, MD.
Rest stop #5 from 12:00PM to 3:00PM at Mile 92, St. Stephens AME Church, 9467 Unionville Rd, Easton, MD.
Rest Stops for 64.5-mile Course Register Here!
Rest Stop #1 from 7:30AM to 11:00am at Mile 22, Adkins Arboretum , 12610 Eveland RD, Ridgely MD.
Rest Stop #2 from 8:30AM to 12:00PM at Mile 40, Talbot Mentors, 108 Maryland Avenue, Easton MD.
Rest Stop #3 from 9:00AM to 3:00PM at mile 51, Oxford-Bellevue Ferry Landing, Ferry Crossing Slip Road, Oxford, MD.
Rest Stops for 38.6-Mile Course Register Here!
Rest Stop #1 from 9:00AM to 1:00PM at Mile 15, Oxford-Bellevue Ferry Landing, Ferry Crossing Slip road, Oxford, MD.
Rest Stop #2 from 9:30AM to 1:00PM at Mile 26, St. Stephens AME Church, 9467 Unionville Rd, Easton, MD.
Scottish Highland Creamery Ice Cream Pit Stop, 9:00AM - 2:00PM
103 South Morris Street, Oxford, MD 21654, for one scoop of your favorite ice cream flavor.
Cycling event website: Tri-County Ice Cream Classic
Cycling event is for/about: Supporting Wounded Warriors & The Harriett Tubman Museum
Cycling event categories: Tri-County ice cream classic 2025 Chesapeake Cycling Club's Spring Road Cycling Event
Cycling event location- Talbot County Community Center 10028 Ocean Gateway Easton, MD 21601
Additional comments about event:
Check In Starts
102.2 Mile Course 7:00AM with 6:30am option
64.5 Mile Course 7:30AM
38.6 Mile Course 8:00AM
Register Here!
Free Stuff: Camelbak water bike bottle to each participant!
Plus free one-way passage on the Oxford-Bellevue Ferry!
Complimentary finish line food and beer:
Tacos by Papuseria Kent Island Food Truck.
Scottish Highland Creamery Ice Cream pit stop.
Live music by New Legacy Blues Band.
NEW FOR 2025!
"The Scoop" Swap & Sell!
Buy, sell, swap, trade . . . It's a classic swap meet!
Admission is FREE to all registered participants.
Those planning to offer items for sale MUST reserve tables in advance. Tables are FREE!
May 10, 2025 from 11:30AM - 3:00PM, at the Talbot County Community Center.
Please email Eric Griffioen HERE to reserve in advance.
Supporting Wounded Warriors & The Harriett Tubman Museum
Rest Stops for 102.2-Mile Course Register Here!
Rest Stop #1 from 7:30AM to 11:00AM at Mile 22, Adkins Arboretum , 12610 Eveland RD, Ridgely MD.
Rest Stop #2 from 8:30:AM to 12:00PM at Mile 40, Talbot Mentors 108 Maryland Avenue, Easton MD.
Rest Stop #3 from 10:30AM to 1:00PM at Mile 63, 3748 Main Street, Trappe, MD.
Rest stop #4 from 11:00AM to 1:30PM at Mile 75, Oxford-Bellevue Ferry Landing, Ferry Crossing Slip road, Oxford, MD.
Rest stop #5 from 12:00PM to 3:00PM at Mile 92, St. Stephens AME Church, 9467 Unionville Rd, Easton, MD.
Rest Stops for 64.5-mile Course Register Here!
Rest Stop #1 from 7:30AM to 11:00am at Mile 22, Adkins Arboretum , 12610 Eveland RD, Ridgely MD.
Rest Stop #2 from 8:30AM to 12:00PM at Mile 40, Talbot Mentors, 108 Maryland Avenue, Easton MD.
Rest Stop #3 from 9:00AM to 3:00PM at mile 51, Oxford-Bellevue Ferry Landing, Ferry Crossing Slip Road, Oxford, MD.
Rest Stops for 38.6-Mile Course Register Here!
Rest Stop #1 from 9:00AM to 1:00PM at Mile 15, Oxford-Bellevue Ferry Landing, Ferry Crossing Slip road, Oxford, MD.
Rest Stop #2 from 9:30AM to 1:00PM at Mile 26, St. Stephens AME Church, 9467 Unionville Rd, Easton, MD.
Scottish Highland Creamery Ice Cream Pit Stop, 9:00AM - 2:00PM
103 South Morris Street, Oxford, MD 21654, for one scoop of your favorite ice cream flavor.
May 23-25, 2025 Farm to Fork - Maryland's Eastern Shore-Weekend Getaway -
Chestertown, MD
Varies daily up to 40 miles
Recreational Bike Tour
2025 Farm to Fork - Maryland's Eastern Shore-Weekend Getaway -
June 2025-
Jun 14, DCXC 2025
Germantown, MD
3 laps, 2 laps, 1 laps, 0 hours
Mountain Bike
DCXC 2025
Jun 28, DIVA CYCLING'S 5th Annual Colors of Cancer Awareness Ride
White Plains, MD
65 miles, 45 miles, 27 miles, 7 hours, 6 hours, 4 hours, 3 hours, 2 hours
Special Event
DIVA CYCLING'S 5th Annual Colors of Cancer Awareness Ride
July 2025-
Jul 7 - Aug 8, 2025 Mini Pedals Mountain Bike Camp
Woodlawn, MD
5 hours
Cycling Camp
2025 Mini Pedals Mountain Bike Camp
Jul 12, Fair Hill Firecracker MTB (Mid-Atlantic Super Series)
Elkton, MD
7 miles, 5 miles, 21 miles, 14 miles, 4 + hours
Mountain Bike Mid Atlantic Super Series
Fair Hill Firecracker MTB (Mid-Atlantic Super Series)
Jul 7 - Aug 8, 2025 Mini Pedals Mountain Bike Camp
Woodlawn, MD
5 hours
Cycling Camp
2025 Mini Pedals Mountain Bike Camp
Aug 16, Big Elk Off-Road XC & Endurance MTB Race @ Fair Hill (Mid-Atlantic Super Series)
Elkton, MD
7 miles, 5 miles, 21 miles, 14 miles, 4 + hours
Mountain Bike Mid Atlantic Super Series
Big Elk Off-Road XC & Endurance MTB Race @ Fair Hill (Mid-Atlantic Super Series)
September 2025-
Sep 13, 3M Bike Challenge
Cumberland, MD
15.6 miles
Gravel
Sep 14, Gran Fondo Maryland Volunteers
Frederick, MD
Gran Fondo Road Race
Sep 14, Gran Fondo Maryland, p/b Ourisman Automotive Group, a Suarez Gran Fondo National Series event
Frederick, MD
97.6 miles, 61.4 miles, 27.8 miles
USA Cycling
Gran Fondo Road Race
Gran Fondo Maryland, p/b Ourisman Automotive Group, a Suarez Gran Fondo National Series event
Dec 16, 2024 - Sep 30, 2025, Kelly Benefits Cycling / Lateral Stress Velo (LSV) 2025 Membership
Baltimore, MD
USA Cycling
Club Membership
Kelly Benefits Cycling / Lateral Stress Velo (LSV) 2025 Membership
October 2025-
Nov 21, 2024 - Oct 31, 2025, Annapolis Bicycle Racing Team (ABRT) Membership 2025
Annapolis, MD
Club Membership
Annapolis Bicycle Racing Team (ABRT) Membership 2025
December 2025-
Jan 17, 2024 - Dec 31, 2025, PHASE Cycling Membership
Largo, MD
Club Member
Chestertown, MD
Varies daily up to 40 miles
Recreational Bike Tour
2025 Farm to Fork - Maryland's Eastern Shore-Weekend Getaway -
June 2025-
Jun 14, DCXC 2025
Germantown, MD
3 laps, 2 laps, 1 laps, 0 hours
Mountain Bike
DCXC 2025
Jun 28, DIVA CYCLING'S 5th Annual Colors of Cancer Awareness Ride
White Plains, MD
65 miles, 45 miles, 27 miles, 7 hours, 6 hours, 4 hours, 3 hours, 2 hours
Special Event
DIVA CYCLING'S 5th Annual Colors of Cancer Awareness Ride
July 2025-
Jul 7 - Aug 8, 2025 Mini Pedals Mountain Bike Camp
Woodlawn, MD
5 hours
Cycling Camp
2025 Mini Pedals Mountain Bike Camp
Jul 12, Fair Hill Firecracker MTB (Mid-Atlantic Super Series)
Elkton, MD
7 miles, 5 miles, 21 miles, 14 miles, 4 + hours
Mountain Bike Mid Atlantic Super Series
Fair Hill Firecracker MTB (Mid-Atlantic Super Series)
Jul 7 - Aug 8, 2025 Mini Pedals Mountain Bike Camp
Woodlawn, MD
5 hours
Cycling Camp
2025 Mini Pedals Mountain Bike Camp
Aug 16, Big Elk Off-Road XC & Endurance MTB Race @ Fair Hill (Mid-Atlantic Super Series)
Elkton, MD
7 miles, 5 miles, 21 miles, 14 miles, 4 + hours
Mountain Bike Mid Atlantic Super Series
Big Elk Off-Road XC & Endurance MTB Race @ Fair Hill (Mid-Atlantic Super Series)
September 2025-
Sep 13, 3M Bike Challenge
Cumberland, MD
15.6 miles
Gravel
Sep 14, Gran Fondo Maryland Volunteers
Frederick, MD
Gran Fondo Road Race
Sep 14, Gran Fondo Maryland, p/b Ourisman Automotive Group, a Suarez Gran Fondo National Series event
Frederick, MD
97.6 miles, 61.4 miles, 27.8 miles
USA Cycling
Gran Fondo Road Race
Gran Fondo Maryland, p/b Ourisman Automotive Group, a Suarez Gran Fondo National Series event
Dec 16, 2024 - Sep 30, 2025, Kelly Benefits Cycling / Lateral Stress Velo (LSV) 2025 Membership
Baltimore, MD
USA Cycling
Club Membership
Kelly Benefits Cycling / Lateral Stress Velo (LSV) 2025 Membership
October 2025-
Nov 21, 2024 - Oct 31, 2025, Annapolis Bicycle Racing Team (ABRT) Membership 2025
Annapolis, MD
Club Membership
Annapolis Bicycle Racing Team (ABRT) Membership 2025
December 2025-
Jan 17, 2024 - Dec 31, 2025, PHASE Cycling Membership
Largo, MD
Club Member
Sep 21st Saturday C3 Rolling Donuts Ride
Cycling event website: http://ridec3.org/
Cycling event is for/about Sweat late season cycling event through the farmlands, water views of Maryland Eastern Shore with a great cycling after event party. Flat, fast, and fun cycling challenge.
Cycling event categories: Four Routes 26 miler, 48 miler, 66 miler, and 105 miler.
Cycling event location: Tuckahoe State Park, Cherry Lane Pavillon, 13283 Cherry Lane Queen Anne MD 21657
Register Now!
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