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Bicycling Events for 2023

in Maryland and Surrounding States

January | February| March | April | May | June | July | August | September | October | November | December
---No events posted for January--
Wednesday
February 8 2023
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 1 2023
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.
Saturday
April 15 2023
Positive Strides Spring Classic Easton MD
25, 50 and 62 mile routes on Maryland's Eastern Shore.
Benefits Positive Strides, formerly 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.
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.
Saturday
April 22 2023
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.
Saturday
April 29 2023
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.
Sunday
April 26
Not listed for 2023
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.
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.
Saturday
May 6 2023
Six Pillars Century Gerry Boyle Park, 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.
Saturday
May 6 2023
Tour de Madison - The Vineyards of Madison County Syria VA
22, 46 and 65 miles.
Presented by Madison County Parks and Recreation.
Saturday
May ??
Not listed for 2023
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.
Saturday
May 6 2023
Rain date May 7
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.
Friday
May 12 or
Saturday
May 13 2023
Cap2Cap Charles City VA
7, 23, 52, 100 miles, 2-day, and virtual options.
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 13 2023
Ride for the Feast Easton MD
42, 66, and 100 mile routes
Benefits Moveable Feast. Raises funds for services and raises awareness of nutritional needs of people living with HIV/AIDS and breast cancer.
Each rider is asked to raise a minimum of $1,000, which is the cost of feeding one client for a full year.
Friday
May 19 2023
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 20 2023
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. Great FLAT routes with views of the water everywhere you turn.
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; The supported ride is Saturday, but there are plenty of activities to make this a weekend event.
Sunday
May 21 2023
Storming of Thunder Ridge Lynchburg VA.
27, 45, 47 (The Mountain 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.
Friday
May 26 -
Monday
May 29 2023
Chestertown Weekend - formerly 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.
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.
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.
Saturday
June 10
2023
Tour de Frederick Frederick, MD. 
Enjoy a cycling weekend to benefits youth through the Boys and Girls 10, 31, 62, and 102 miles and kids' rodeo on Saturday, followed by a finish-line party. Riders may register individually or as teams.
The tour benefits the Boys & Girls Club of Frederick County and many other local non-profits.
Sunday
June 11 2023
Firefighter 50 Bike Ride Pleasant Valley MD (6 miles west of Westminster MD).
35, 50, 62 and 100 miles through Carroll and Frederick Counties in Maryland and Adams County in Pennsylvania.
Benefits the Pleasant Valley Fire Department in Westminster, MD.
Includes all-you-can-eat firefighter lunch. T-shirts available on the event day.
Sunday
June 11 2023
Loudoun 1725 Gravel Grinder Middleburg VA
40, 60, or 80-mile routes along historic gravel roads in Northern Virginia. Ride on the largest and oldest intact network of gravel roads in the United States, which have been in use since the early 1700s, past horse farms, wineries, bubbling creeks, tiny hamlets, and significant historical sites. The ride will be fully marked and supported, with well stocked rest stops, mechanical and SAG support.
5% of gross ride funds will be donated to America�s Routes, a group that is advocating to save these historic rural roads from being paved over by development. Riders may donate additional funds during registration. Registration fees vary by distance ridden. A tri-blend t-shirt may be purchased for $15 and post-race meal with one craft beer or soda is $15.
Sunday
June 11 2023
Bike-a-thon Bridge to the Beach Philadelphia PA to Atlantic City NJ
Saturday
June 15
Le Tour de Shore Onancock, VA.
Friday
June 23-
Wed
June 28 2023
Bike Virginia Tour  Staunton VA and Harrisonburg VA.
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
Saturday
June 17 2023
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 fee varies by distance
Sunday
June 25 2023
Bay to Bay Jim Gent Memorial Ride Betterton MD
26, 50, 85, or 102 miles flat. The 26-mile ride is a loop through Historic Chestertown. Start from Betterton Volunteer Fire Company.
Presented by the Chestertown Lions Club with proceeds to benefit Lions Club Leader Dog Program for the Blind. All blind riders may ride free.
Includes map, marked routes, gift (first 450 riders to register), sag, six food stops.
Saturday
June 24 2023
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.
Sunday
June 28
Northern Virginia Tour de Cure Reston, VA.
VIRTUAL EVENT
Saturday
July 8 -
Tuesday
July 11 2023
The Great 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.
Your registration fee and pledges (see web site for details) 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 23 2023
Heart of the Chesapeake Bike Tour Cambridge MD
32 miles through Dorchester County; 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.
Saturday
Aug 1
Chocolate Tour Hershey, PA.
VIRTUAL EVENT
Saturday
Aug 5 2023
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.
Sunday
Aug 20 2023
The Lancaster Covered Bridge Classic Lancaster PA
35, 50, 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.
Seven start locations are offered. Registration ends at 2,200 riders.
Sunday
Aug 20 2023
Reston Century Reston Town Center, Reston VA.
31, 60, 80 and 100 miles. Presented by the Reston Bicycle Club with proceeds benefiting various local support and non-profit organizations. Limit of 1,500 riders.
Saturday
August 26 2023
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.
Saturday
August 29 2023
Iron Furnace Fifty Snow Hill MD.
50-mile route 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.
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
September 9 2023
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 shortcut 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.
Saturday
Sept 9
Amish Country Bike Tour Legislative Mall, Dover, DE
16, 25, 50, 62 and 100-mile routes 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 13
2022
Shenandoah Valley Century Harrisonburg, VA .
Sunday
Saturday
Sept 21
Cycling for Perry Point Fisher House Ride Perry Point, MD.
Saturday
Sept ?? ????
Taking a break in 2023
Shorebird Metric Century Wicomico 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.
Sunday
Sept 17 2023
Ride for Clean Rivers Chesapeake College, 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.
Registration includes event T-Shirt.
Sunday
Sept 22
Back Roads Century Shepherdstown, WV.
Saturday
September ??
St. Mary’s Century Mechanicsville, MD.
Not scheduled in 2023
Saturday
Sept 16 2023
Ride for the River Riverfront Park, 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.
Saturday Sept 16 2023 Cannonball Century Lake Anna Winery, Spotsylvania VA.
36, 63 or 100 mile routes over flat to fairly hilly roads through scenic central Virginia.
Presented by the Fredericksburg Cyclists Club with a portion of the event proceeds going to area charities.
Sunday
Oct 1 2023
Anne Arundel County 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.
Saturday
Oct 14 2023
Seagull Century Salisbury University, Salisbury MD
62 and 100 miles. Registration opens in June. Proceeds benefit dozens of non-profit organizations.
$100 until September 1; $130 until September 20. Includes long-sleeve t-shirt.
Saturday
Oct 12 2019
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.
16, 26, 38 or 62 miles through Baltimore County to remember Larry Bensky, who was struck by a car and killed while bicycling, and to bring attention to the need for increased driver awareness on our roads in Maryland.
This is a fund-raising event for Bike Maryland, the state-wide advocac organization whose mission is to promote bicycling, increase safety, improve conditions, and provide a voice for bicyclists in Maryland.
$40; $20 for youth under 16.
Saturday
Oct 28 2023
Between the Waters Bike Tour Exmore, VA.
25, 40, 60 or 100 miles along golden marshes, pastoral fields, and through hidden, bayside hamlets.
Presented by the Citizens for a Better Eastern Shore, a non-profit organization dedicated to promoting balanced growth, enhancing the quality of life of all our citizens, and preserving our cultural and natural resources. .
BIKE TOUR FEES*:
Adult $81.00
Children (6 -12 yrs) $20
Under 6 free with an adult
*LATE FEE $10 as of AUGUST 1st
NO REFUNDS --- NO Transferring Registrations
---No events posted for November---
Saturday
Nov 2 2019
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 Connect�s 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 for December---
































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


 

Oxon Hill Bicycle and Trail Club
P.O. Box 81  
Oxon Hill, MD 20750-0081

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