Bicycling Events for 2019

in Maryland and Surrounding States

January | February| March | April | May | June | July | August | September | October | November | December

--No events posted for January--
Tuesday
February 19
Maryland Bicycle 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. 7:00 AM to 3:30 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 13
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 17; $25 March 17 to April 7; $30 on the day of the ride.
Saturday
April 13
TSR Spring Classic Easton, MD.
25, 50 and 62 mile routes on Maryland's Eastern Shore.
Benefits Talbot 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 or $55.
Saturday
April 20
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 April 18.
Saturday
April 27
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 before April 1, then $59.  Includes t-shirt.
Saturday
April 27
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 yearís event will feature special anniversary celebrations.
Presented by the Bethany-Fenwick Area Chamber of Commerce.
$55 by Feb. 28; $60 by Mar. 31; $75 before the close of online registration April 19. 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.
Saturday
April 27
Hampton Roads Tour de Cure Suffolk, VA.
12, 30, 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. Fundraising minimum is $200.
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 4
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. Event tee shirt to first 1,000 to register.
Saturday
May 4
Shorebird Century Parsonsburg, MD.
15, 35, and 65 mile routes on the lightly traveled roads of the Eastern Shore through Maryland and Delaware. This year's ride, as in past years, is in honor and memory of all who have been touched by cancer. Limit 500 riders.
$45.00 until April 13th, then $55. Net proceeds raised benefit the American Cancer Society and their cancer fighting mission.
Saturday
May 4
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 4/14/19) and a cinch bag. One child 12 or younger rides FREE with paid adult entry -- additional children are $20 each.
Saturday
May 11
Cap2Cap Charles City, VA.
7, 23, 52 and 100 miles.
Benefits the Virginia Capital Trail Foundation.
Registration fees vary by ride distance and rider age; see website for details.
Registration includes t-shirt, drawstring bag and water bottle.
Saturday
May 11
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 28, $59 from March 1-April 30, $70 from May 1-11. Includes t-shirt if pre-registered by April 30. Luncheon provided at Furnace Town after the ride, with entertainment and complementary beverages.
Saturday
May 11 -
Sunday
May 12
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.
$135 ($120 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. 100% of what is raised will go directly to client services.
Friday
May 17
Bike to Work Day Washington, DC.
The Metropolitan Washington Council of Governments and the Washington Area Bicyclist Association invite you to celebrate bicycling as a clean, fun and healthy way to get to work. Register early for a pit stop near your home or work to show your support for bicycling and reserve your free Bike to Work Day t-shirt. Then on Bike to Work Day, stop by your pit stop to pick up your t-shirt and enjoy breakfast treats, prizes, and more. Registration opens in March.
Saturday
May 18
DC Bike Ride Washington, DC.
20 scenic miles, riding past some of DC's most iconic sights and finishing on Pennsylvania Avenue in the shadow of the U.S. Capitol. This event is for all ages (3+) and all riding abilities. The ride ends with a festival between the U.S. Capitol and the National Mall that includes entertainment, family-friendly activities, beats and eats.
Proceeds will benefit WABA's street safety programs in support of DC's Vision Zero Campaign.
Registration opens January 30.
Saturday
May 18
Tour de Chesapeake Mathews, VA.
23, 24, 25 and 30 miles; ride one or more routes. Do all four routes for a 103-mile century.
Presented by the County of Mathews, the Mathews Land Conservancy, and the Mathews Visitor Center to celebrate the arrival of spring with a weekend of scenic cycling; great FLAT routes with views of the water everywhere you turn. The supported ride is Saturday, but there are plenty of activities to make this a weekend event.
Saturday
May 18
Tour de Madison - The Vineyards of Madison County Syria, VA.
20, 45 and 65 miles, with shorter family rides from the Graves Mountain Lodge, 20 miles west of Culpeper, VA. Presented by Madison County Parks and Recreation.
$40 for Metric Century and Intermediate riders who register before May 4; after May 4 is $55.  For Family riders the fee is only $20 before May 4, after May 4, $35.   On site registration is $55 for Metric Century and Intermediate Riders and $35 for Family Riders.
Sunday
May 19
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 raise funds for the YMCA of Central Virginia's Annual Fund.
$70 before May 1; $80 after May 1. 27 miler deduct $15. Online registration ends at noon on May 19. Registration includes a SOTR cotton t-shirt (guaranteed to those pre-registered prior to May 1st). Free outdoor camping; indoor camping for $10.
Friday
May 24 -
Monday
May 27
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 May 1st; $50 May 1st through May 15; no refunds after May 15;
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 1
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 the Co-opís corporate charities for 2019, three local organizations that help people with disabilities: Spring Dell Center in Charles County, The Arc of Southern Maryland in Calvert County; and Bay Community Support Services in St. Maryís County.
$40 until May 2; $50 from May 3 to May 25; $55 from May 26 to day of ride. Register before May 2 to receive a commemorative t-shirt.
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 2
Maryland Tour de Cure Baltimore, MD.
13, 29 and 63 miles over the gently rolling countryside of Western Howard County to raise funds for the American Diabetes Association.
Registration fee is $15. In addition to registration fee, riders must raise a minimum of $200.
Sunday
June 2
Northern Virginia Tour de Cure Reston, VA.
20, 35, 55 and 106 miles from Reston Town Center.
Presented by the American Diabetes Association to raise money for diabetes research, advocacy and educational programs.
$10.00 for early registration through January 31 and fundraising minimum of $250. Riders receive a commemorative Tour de Cure T-shirt.
Sunday
June 9
Bike-a-thon Bridge to the Beach Philadelphia, PA to Atlantic City, NJ.
Six route options from four start-points, including a century, through scenic back roads of South Jersey ending on the Boardwalk in Atlantic City to raise funds for the American Cancer Society.
$40 with an additional $100 fundraising minimum. Registration increases to $60 on February 1, $80 on April 1 and $100 on June 1.
Saturday
June 15
Le Tour de Shore Onancock, VA.
15, 30, 62 and 100 miles on the flat Eastern Shore.
Presented by the Eastern Shore of Virginia Chamber of Commerce.
$55 through April 12. $65 by noon on June 14, $75 on site. ($3 processing fee added per ticket for online sales.) Jerseys are included for the first 150 riders. Sizes cannot be guaranteed after May 1.
Friday
June 21-
Wed
June 26
Bike Virginia Tour 2019  Woodstock, VA and Harrisonburg, VA.
Bike-o-Rama Multiple routes with up to 400 miles of riding options offered in loop routes of 10-100 miles. Riders may register for 1 day, a weekend, or 6 days of cycling. Camping and hotels are available for lodging. Nightly entertainment with beer and wine gardens, food trucks with many options including vegetarian dishes, rest stops with refreshments about every 20 miles hosted by local community organizations.
Registration fees vary and increase on February 1.
Saturday
June 22
Garrett County Gran Fondo McHenry, MD
25, 44, 65, 106 and 126 miles. This Gran Fondo is a long distance, mass-participation, cycling event. The 25 mile route goes along Deep Creek Lake and through the rolling Garrett County farmland. The longer routes include many challenging climbs, with 16,500 feet of elevation gain for the 126 mile "Diabolical Double."
Benefits the Garrett Trails Non Profit Organization and their mission to build the Eastern Continental Divide Loop.
Registration varies by distance and ends June 10 at 5 pm.
Saturday
June 29
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 June 2; $25 through June 23; $30 on day of ride.
Saturday
July 13 -
Tuesday
July 16
The Greatest Bicycle Tour of the Historic C&O Canal
Almost 200 miles on the C&O Canal. No hills, no headwinds, & no cars.
Benefits the San Mar Children's Home in Boonsboro, Maryland.
$40 registration fee ($55 after June 30) and minimum fundraising of $475 ($425 for those riding for only the weekend). For those exceeding minimum amounts there are prizes awarded for going above and beyond. Your registration fee and pledges provide transportation by charter bus to the start of the C&O Canal, all meals and snacks, free parking for your vehicle throughout the event, rest stops every ten to fifteen miles, camp fees paid for the first two nights or transportation to nearby hotels, hotel on the third night, transport of all gear throughout the event, T-shirt, water bottle, a TGBT patch, and return to your vehicle by charter bus from Georgetown at end of 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 20
Heart of the Chesapeake Bike Tour Cambridge, MD.
32, 52 and 66 miles through Dorchester County; all rides are flat and in low-traffic areas.
Sponsored by the Dorchester County Family YMCA to benefit the Dorchester YMCA Bob Brannock Endowment Fund and the Y's Scholarship Fund.
$40, increasing after February 28. $5 per-person discount for groups of 4 or more riders.
Sunday
July 21
Firefighter 50 Bike Ride Pleasant Valley, MD (6 miles west of Westminster, MD).
35, 50 and 100 miles through the beautiful countryside of 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 3
Chocolate Tour Hershey, PA.
10, 30, 50, 75 and 100 miles through central Pennsylvania with its Amish farms, wooded areas, and covered bridges while visiting the historic chocolate towns of Hershey (home of Hershey's Chocolate), Elizabethtown (home of M and M Mars), and Lititz (home of Wilbur Chocolate Company).
All funds raised by the Chocolate Tour support cancer research at Penn State Hershey Cancer Institute.
$45 through July 7; $55 from July 8 to July 27; $65 on the day of the ride.
Saturday
Aug 9-
Sunday
Aug 11
Tour de Frederick Frederick, MD. 
Enjoy a cycling weekend to benefits youth through the Boys and Girls Club of Frederick County and the Rotary Club of Carroll Creek.
10, 31, 62, and 102 miles and kids' rodeo on Saturday, followed by a finish-line party. The Frederick History Ride through downtown is on Sunday morning.
$85 through August 8; $100 on site. Riders may register as teams with $200 fundraising per team member (no fundraising required for solo riders).
Saturday
Aug 10
Shorefire Century Middletown, DE.
35, 65, and 100 miles through flat to gently rolling farmland in central Delaware.
Presented by the White Clay Bicycle Club.
$20 through July 14; $25 through August 4; $30 on day of ride.
Sunday
Aug 18
The Lancaster Covered Bridge Classic Lancaster, PA.
16, 33, 65 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.)
Registration will open 1/1/2018.
$40 before March 1, $50 from March 1-June 30, $60 after July 1. Registration ends Friday August 16 or at 2,200 riders.
Saturday
Sept 7
BBC Civil War Century Thurmont, MD.
25, 51, 64, 75 and 102 miles. Visit famous historical sites while enjoying low traffic roads and breathtaking scenery. The 25-mile beginner route crosses three covered bridges, while the longer routes visit the Gettysburg battlefield site. The challenging, hilly century route also visits the Crampton's Gap, South Mountain and Antietam battlefield sites. Presented by the Baltimore Bicycling Club.
Registration will open in early June and is limited to 1600 riders.
Saturday
Sept 7
Amish Country Bike Tour Dover, DE.
15, 25, 50, 63 and 100-mile loops through the flatlands of Delaware's Amish farmlands. All ages and abilities; rest stops including the famous Amish school house where the Amish serve homebaked pies and cookies. Plenty of healthy food stops. After-tour party, live music, yard games and catered picnic.
Sponsored by Kent County Tourism to benefit local non-profit organizations.
Sunday
Sept 8
Shenandoah Valley Century Harrisonburg, VA .
Presented by the Shenandoah Valley Bicycle Coalition. Proceeds support the coalition's mission to build better communities in the Valley.
Sunday Sept 29 Cannonball Century Hartwood, VA.
30, 67 or 102 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.
Saturday
Oct 5
Seagull Century Salisbury, MD.
62 and 100 miles. Registration opens in May. Proceeds benefit dozens of non-profit organizations.
Sunday
Oct 6
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; add $5 from June 1 to ride day. $30/$35/$50/$60 for walk-in registration on the day of the ride.
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
Nov 2
Lime Connect Century Reston, VA
102, 66 or 30 miles in Fairfax and Loudoun Counties. The Lime Connect Century Ride will bring together passionate riders and supporters for a scenic ride across Northern Virginia for a great cause: forging a pathway to success in the corporate workplace for students and professionals - including veterans - with disabilities. 100% of all proceeds raised will go toward Lime Connectís mission to rebrand disability through achievement. Riders of all levels are welcome.
Century Ride: $120, Metric Century: $80, 30 Mile: $60. Price increases after September 10.
--No events posted yet for December--
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
   

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