Bicycling Events for 2020

in Maryland and Surrounding States

January | February| March | April | May | June | July | August | September | October | November | December
 
---No events posted for January--
Wednesday
February 19
Bike Maryland Symposium Annapolis, MD.
Bike Maryland presents the annual Maryland Bicycle Symposium. Learn from leaders in the bicycling field, bicycling advocates, planners, community leaders and legislative officials on current topics with the goal of increasing bicycle safety, connectivity and accessibility. 8:00 AM to 4:00 PM at the President's Conference Center West in the Thomas V. Mike Miller, Jr. Senate Building, 11 Bladen Street, Annapolis, MD 21401. The event is free and open to the public.
---No events posted for March---
Saturday
April 4
Icicle Metric Century Elkton, MD.
13, 24 and 31 mile loops that can be combined for up to 68 miles in moderately hilly terrain in the areas west and north of Newark, Delaware. Sponsored by the White Clay Bicycle Club.
$20 to March 8; $25 to March 29; $30 on the day of the ride.
Saturday
April 18
Canceled due to covid-19
Positive Strives Spring Classic Easton, MD.
25, 50 and 62 mile routes on Maryland's Eastern Shore.
Benefits Positive Strives, formerlyTalbot Special Riders, a volunteer driven non-profit which provides equine therapy to developmentally disabled individuals in and around Talbot County on Maryland's Eastern Shore.
$45 through February 15, then price increases.
Saturday
April 18
New Holland Bicycle Race New Holland, PA.
30 & 50+miles ride/race. (2500 - 4300 ft of climb) Bike & Cash prizes. Scenic Lancaster County, Pennsylvania. Rolling hills and No traffic.
$45 prior to April 18.
Saturday
April 25
Postponed until Sat., Sept. 12
Ride to End Hunger in Calvert County Huntingtown, MD.
16, 35, 48 and 63 miles on the scenic Western Shore of the Chesapeake Bay. Pedal along the bayfront and past marinas, farmland and a local winery.
Sponsored by End Hunger in Calvert County with proceeds going to food pantries in Calvert County.
$39 before March 1, $49 during March, then $59.  Includes t-shirt.
Saturday
April 25
Postponed
Ocean to Bay Bike Tour Bethany Beach, DE.
30, 50, 62 and 100 miles through the beautiful coastal and inland bay areas of Sussex County, Delaware. Celebrating 30 years, this year’s event will feature special anniversary celebrations.
Presented by the Bethany-Fenwick Area Chamber of Commerce.
$60 by March 1; $65 by April; $75 before the close of online registration April 17. Team discount for six or more cyclists on a team. Select the combo option for an additional $15 to add the 15-mile Friday Fun Ride.
Sunday
April 26
?
Draw For Sight Bicycle Poker Run Ride Betterton, MD
36 and 60 miles from the Betterton Firehouse. Rolling to flat routes takes in the scenery of the heartland of Upper Kent County in Maryland including farmlands, old country homes, quaint towns, and great country stores. The ride goes through historic Chestertown.
Benefits Lions Club sight projects.
$25 until March 31; $30 April 1 until April 25; $40 Day of Ride.
Sunday
April 28
Powhatan Historic Bike Tour Powhatan, VA.
35, 62 and 100 miles from Powhatan Courthouse Village (30 miles west of Richmond). 
Benefits the Free Clinic of Powhatan, which provides high quality medical, dental, and mental health care services at no cost to Powhatan County's uninsured, low-income residents. 
$35 for the 35 mile route;  $45 for the 100km (62 mile) metric century; $55 for the 100 mile century.  After February 15, registration fees increase to $40, $50 and $60. After April 1, $45, $60 and $70. Registration fee includes t-shirt or unique finisher's medal.  Optional biker's breakfast is $6. 
Saturday
May 2
Postponed
Six Pillars Century Cambridge, MD.
37, 56 and 100 miles from Great Marsh Park with most of the miles through the Blackwater National Wildlife Refuge. Sponsored by Character Counts Mid Shore, Inc., a non-profit education organization that fosters positive character development for students in grades K-12.
$60 increasing to $65 in March.
Saturday
May 2
Postponed to Sat, June 20
Hampton Roads Tour de Cure Suffolk, VA.
12, 30, 50, 62 and 100 miles through the peaceful peanut countryside of Suffolk, Virginia, past horse farms and scenic lakes.
A fundraiser for the American Diabetes Association.
Registration fee is $20 to February 22, then $30. Fundraising minimum is $250.
Saturday
May 2
Canceled
Tree House Tour de Cookie Rockville, MD.
12, 27 and 43 miles from the Johns Hopkins Montgomery County Campus.The shorter route is mostly on the Millennium Trail - a paved off-road shared-use path. 
All proceeds will benefit the Tree House Child Advocacy Center of Montgomery County. 
$60 ($55 for member of a team of 10 or more). Participants will receive a moisture wicking t-shirt if registered before 4/12/19 and a cinch bag. One child 12 or younger rides FREE with paid adult entry -- additional children are $20 each.
Saturday
May 9
Postponed to Sat, August 22
Cap2Cap Charles City, VA.
7, 23, 52 and 100 miles.
Benefits the Virginia Capital Trail Foundation.
Century fee is $60 to 11/11/19; $70 to 1/3;$80 to 2/7; $90 to 4/3.
Half and quarter century $55 to 11/11/19; $65 to 1/3;$75 to 2/7; $85 to 4/3.
Family Fun Ride fee is $25 to 11/11/19; $30 to 1/3;$35 to 2/7; $40 to 4/3.
Youth (ages 12-17) $35 to 11/11/19; $40 to 1/3;$40 to 2/7; $50 to 4/3.
Youth (11 and under) $10 to 11/11/19; $10 to 1/3;$15 to 2/7; $20 to 4/3.
Registration fees vary by ride distance and rider age; see website for details.
Registration includes t-shirt, drawstring bag and water bottle.
Saturday
May 2 -
Sunday
May 3
Postponed
Ride for the Feast Ocean City, MD to Baltimore, MD.
140 miles in two days.
Benefits Moveable Feast. Raises funds for services and raises awareness of nutritional needs of people living with HIV/AIDS and breast cancer.
$110 ($85 for returning riders) includes t-shirt, water bottle and six meals. Each rider is asked to raise a minimum of $1,500, which is the cost of feeding one client for a full year.
Saturday
May 9
Postponed to Sat, August 29
Iron Furnace Fifty Snow Hill, MD.
34, 50 and 62 mile routes on Maryland's Lower Eastern Shore, starting and ending at Furnace Town Living Heritage Village (between Snow Hill and Salisbury). Enjoy cycling on flat terrain on sparsely travelled roads through the Great Pocomoke Forest and surrounding farmland. Free farm fresh ice cream from local working dairy on all routes.
Proceeds benefit Furnace Town Living Heritage Village and Rotary Club of Snow Hill.
$52 until February 29th; $59 from March 1-April 30th; $70 from May 1-May 9th.
Early TEAM Registration ( 6 or more members )$45/per rider; Advance TEAM Registration $52/per rider; Regular TEAM Registration $65.
Includes t-shirt if pre-registered by April 25.
Friday
May 15
Canceled
Bike to Work Day Washington, DC.
Commuter Connections and the Washington Area Bicyclist Association invite you to celebrate bicycling as a clean, fun, and healthy way to get to work. Be one of the first 20,000 to register and attend this FREE EVENT, then bike to your choice of 115 pit stops in DC, MD, and VA and receive a free T-shirt, refreshments, and be entered into a raffle for a new bicycle. .
Saturday
May 16
Postponed to Fall
DC Bike Ride Washington, DC.
20 miles from West Potomac Park on Ohio Drive SW just south of 121 West Basin Drive SW in Washington, DC. The course will be closed to all car-traffic. There will be a shorter course available as well, around 6 miles, with a short cut back to the Finish Festival. The ride finishes on 3rd St SW between the U.S. Capitol and the National Mall with a festival that goes until 12:30pm
Proceeds will benefit WABA's street safety programs in support of DC's Vision Zero Campaign.
Registration opens February 5
Saturday
May 16
Canceled
Tour de Chesapeake Mathews, VA.
Saturday
May 16
Canceled
Tour de Madison - The Vineyards of Madison County Syria, VA.
Sunday
May 17
Canceled
Storming of Thunder Ridge Lynchburg, VA.
27, 45, 47 (The Mountatin Only), 75 and 100 miles in the Blue Ridge Mountains.
Sponsored by the YMCA of Central Virginia to helps fund the Community Support Campaign of the YMCA of Central Virginia.
$75 before May 1; $80 after May 1. 27 miler deduct $15. Price increases on May 1. Online registration ends at noon on May 15.
Friday
May 22 -
Monday
May 25
Canceled
Kent County Spring Fling Chestertown, MD.
11 to 100 miles on Maryland's Eastern Shore. Cycle along flat to rolling, lightly traveled roads, by rural hamlets and along scenic rivers. Both riders and non-riders can also enjoy historic Chestertown's annual Tea Party festival - living history, parade, music, food, crafts and boat race.
Presented by BBC (Baltimore Bicycling Club). This 4-day event from Friday to Memorial Day Monday (with an option of 3 days) includes award winning cuisine, dessert and cordial parties, dancing, and great music.
$30 prior to April 15; $50 April 16 to April 22; no refunds after April 22.
Saturday
May 25
Pedal for the Pig Smithfield, VA.
32, 50 and 62 miles through Isle of Wight and Surry County.
Peninsula Bicycling Association (PBA)'s annual spring metric
$59 early-bird registration ($39 for children 12 and under); includes T-shirt and one-year PBA membership.
Saturday
June 6
Postponed until Sat., October 17
SMECO 75 Hughesville, MD.
29, 47 and 75 mile routes through scenic Southern Maryland. Travel through the byways of Southern Maryland to Colton's Point on the shores of the Potomac River.
Presented by the Southern Maryland Electric Cooperative (SMECO). This year's event will benefit organizations in Southern Maryland working to end the opioid crisis.
$50 until May 1; $60 from May 2 to May 28; $75 from May 29 to day of ride. Register before May 1 to receive a performance-wear jacket.
Saturday
June 1
SOAR for Veterans Easton, MD
25, 50 and 63 miles on the Eastern Shore to celebrate our nation's veterans and raise funds to support the Mid-Shore Recovering Veterans Group (MSRVG), a 501(c)(3) nonprofit organization. Funds raised by MSVRG go directly to support veterans through the Mid-Shore Community Foundation.
Saturday
June 1
Broad Creek Bike & Brew Laurel, DE.
15-mile, 25-mile, 50-mile, Metric or Century routes. Cycle through scenic byways and along historic waterways, including historic attractions and a stop at the Trap Pond State Park. Featuring multiple microbreweries and live music at the finish party. Presented by the Laurel Chamber of Commerce to benefit Nanticoke Health Services.
See website for registration information.
Sunday
June 14 Postponed until Sunday, Oct. 25
Loudoun 1725 Gravel Grinder Middleburg, VA
Sunday
June 14
Postponed until Sun., August 9
Bike-a-thon Bridge to the Beach Philadelphia, PA to Atlantic City, NJ.
Saturday
June 15
Le Tour de Shore Onancock, VA.
Friday
June 21-
Wed
June 26
Bike Virginia Tour 2019  Woodstock, VA and Harrisonburg, VA.
Saturday
June 27
Canceled
Garrett County Gran Fondo McHenry, MD
Sunday
June 23
Bay to Bay Ride Betterton, MD.
Saturday
June 27
Canceled
Doublecross Metric Smyrna, DE.
31 and 62 miles. Many bicycle rides cross states that are measured in hundreds of miles and many days. The White Clay Bicycle Club offers an alternative that is modest in time, effort and stamina (a bicycle ride nearly anyone can do) that crosses and doublecrosses an entire state in only 31 total miles over flat terrain. In addition to the traditional route, the event offers a 62-mile (metric century) route for those who would like a longer ride.
$20 through May 31; $25 through June 21; $30 on day of ride.
Sunday
June 28
Northern Virginia Tour de Cure Reston, VA.
VIRTUAL EVENT
Saturday
July 11 -
Tuesday
July 14
The Greatest Bicycle Tour of the Historic C&O Canal
VIRTUAL EVENT
Saturday
July 14
New Holland Bicycle Race New Holland, PA.
Race it or Ride it. Do it for the time or the challenge.  The first half of the course has big rolling hills and fast descents with one good climb to the top of Welsh Mountain.  From Welsh Mtn intermediate cyclists can cut out and coast downhill  5 miles to the start. The second part of the course has stronger climbs and faster descents. Cash/Prizes for 1st, 2nd, 3rd, 4th and 5th.
$45 prior to July 12.
Saturday
July 18
Canceled
Heart of the Chesapeake Bike Tour Cambridge, MD.
Sunday
July 19
Canceled
Firefighter 50 Bike Ride Pleasant Valley, MD (6 miles west of Westminster, MD).
35, 50 and 100 miles through Carroll and Frederick Counties in Maryland and Adams County in Pennsylvania. There is also the Dirty 30 which is a combination of paved and dirt roads.
Benefits the Pleasant Valley Fire Department in Westminster, MD.
$35 ($40 on day of the ride) includes all-you-can-eat firefighter lunch. Optional t-shirt for $15.
Saturday
Aug 1
Chocolate Tour Hershey, PA.
VIRTUAL EVENT
Saturday
Aug 7-
Sunday
Aug 9
Tour de Frederick Frederick, MD. 
VIRTUAL EVENT
Saturday
Aug 8
Shorefire Century Middletown, DE.
Sunday
Aug 16
The Lancaster Covered Bridge Classic Lancaster, PA.
15, 31, 62 and 100 miles through some of Pennsylvania's most famous rural scenery. Each route traverses through covered bridges and past Amish farms. Presented by the Lancaster Bicycle Club with proceeds going to their grants program. (This ride was formerly the Covered Bridge Metric Century.)
$40 before March 1, $50 from March 1-June 30, $60 after July 1. Registration ends Friday August 16 or at 2,200 riders.
Sunday
Aug 23
Canceled
Reston Century Reston, VA.
August 29
Postponed from May 8
Iron Furnace Fifty Snow Hill, MD.
34, 50 and 62 mile routes on Maryland's Lower Eastern Shore, starting and ending at Furnace Town Living Heritage Village (between Snow Hill and Salisbury). Enjoy cycling on flat terrain on sparsely travelled roads through the Great Pocomoke Forest and surrounding farmland. Free farm fresh ice cream from local working dairy on all routes.
Proceeds benefit Furnace Town Living Heritage Village and Rotary Club of Snow Hill.
$52 until February 29th; $59 from March 1-April 30th; $70 from May 1-May 9th.
Early TEAM Registration ( 6 or more members )$45/per rider; Advance TEAM Registration $52/per rider; Regular TEAM Registration $65.
Includes t-shirt if pre-registered by April 25.
Saturday
Sept. 12
Postponed from Sat., April 25
Ride to End Hunger in Calvert County Huntingtown, MD.
16, 35, 48 and 63 miles on the scenic Western Shore of the Chesapeake Bay. Pedal along the bayfront and past marinas, farmland and a local winery.
Sponsored by End Hunger in Calvert County with proceeds going to food pantries in Calvert County.
$49 before August 1; $59 during the month of August & September. Includes t-shirt.
Saturday
Sept 12
Canceled
BBC Civil War Century Thurmont, MD.
Saturday
Sept 12
Amish Country Bike Tour Dover, DE.
Sunday
Sept 13
Shenandoah Valley Century Harrisonburg, VA .
Sunday
Saturday
Sept 21
Cycling for Perry Point Fisher House Ride Perry Point, MD.
Saturday
Sept 19
Shorebird Century Wocoomico Yacht Club, Eden, MD.
15, 35, and 65 mile routes on the lightly traveled roads of the Eastern Shore through Maryland and Delaware.
Proceeds benefit the American Cancer Society.
$45.00 until August 15 includes t-shirt, $55 after August 15th.
Sunday
Sept 20
Ride for Clean Rivers Wye Mills, MD.
20, 35 and 62 miles through the beautiful flat countryside and historic towns of Talbot and Queen Anne's Counties on the Eastern Shore of Maryland. Starts and ends at Chesapeake College on the Wye River in Queen Anne County.
All proceeds go toward ShoreRivers science-based education, restoration, and water quality monitoring programs.
Riders will be required to fill out a screening form the day of the event, but prior to arriving on campus. Chesapeake College will be conducting temperature screening upon arrival to campus. Strict social distancing guidelines will be incorporated throughout the event. This event will move to ride-on-your-own if necessary.
$50 Early Bird (July). $60 On-Time Bird (August). $70 Fashionably-Late Bird (September and day-of registration). $15 Youth (under 18).
Registration includes event T-Shirt (must register by September 9, 2020)
Sunday
Sept 22
Back Roads Century Shepherdstown, WV.
Saturday
Sept 26
St. Mary’s Century Mechanicsville, MD.
Saturday
Sept 28
Ride for the River Pottstown, PA.
16 and 35 mile routes along the Schuylkill River Trail, from Pottstown to Reading, beginning and ending at the Sly Fox Can Jam Festival, where riders can enjoy complimentary food and beer and 8 hours of free live music.
Proceeds benefit the Schuylkill River Greenways NHA.
$45 until September 15, then $55.
Saturday Sept 26 Cannonball Century Hartwood, VA.
32, 63 or 100 mile routes over flat to fairly hilly roads through scenic central Virginia from Curtis Memorial Park.
Presented by the Fredericksburg Cyclists Club with a portion of the event proceeds going to area charities.
$45 through August 16th, $55 through September 11th and $65 onsite "day of" registration. Extra cost for Royal-Blue performance T-shirts, men's crew-neck & women's V-neck.
Saturday
Oct 4
Lifeline 100 Millersville, MD.
15, 30, 60 and 100 miles, and free bike rodeo for children. Presented by The Anne Arundel County Police, the Department of Recreation and Parks and Advocates for Annapolis and Anne Arundel County (BikeAAA).
Proceeds benefit Anne Arundel County non-profits.
$20/$25/$35/$45 for 15/30/62/100 miles before June 1.
$25/$30/$40/$50 June 1 to September 28.
$30/$35/$50/$60 after September 28 and on the day of the ride.
Saturday
Oct 10
Seagull Century Salisbury, MD.
VIRTUAL EVENT
Saturday
Oct 12
New Holland Bicycle Race New Holland, PA.
30, 50 and 82 mile loops in scenic Lancaster County, PA.  Race it or Ride it. Do it for the time or the challenge.  The first half of the course has big rolling hills and fast descents with one good climb to the top of Welsh Mountain.  From Welsh Mtn intermediate cyclists can cut out and coast downhill  5 miles to the start. The second part of the course has stronger climbs and faster descents. Cash/Prizes for 1st, 2nd, 3rd, 4th and 5th.
$45 prior to Oct 10.
Sunday
Oct 13
unPAved of the Susquehanna River Valley Lewisburg, PA.
30, 54 and 90 and 120 mile routes on crushed stone rail trail, dirt, gravel and paved roads through the forest hills and farm country of Central Pennsylvania. The three longer routes include significant climbing.
Registration fee varies by distance. Registration opens March 17 and is limited to 150 riders per distance.
Saturday
Oct 19
Larry's Ride Oregon Ridge Park, Cockeysville, MD.

Submit an Event
If you know of bicycling event of interest to Maryland cyclists, or have comments or suggestions, email ohbikeevents@gmail.com