Oxon Hill Bicycle and Trail Club

Bicycling Events for 2026

in Maryland and Surrounding States

	-- No events posted for January --
Tuesday February 17 2026	Bike Maryland Symposium Annapolis MD Bike Maryland presents the annual Maryland Bicycle Symposium. Miller Senate Office Building, 11 Bladen St, Annapolis, MD
	-- No events posted for March --
Saturday April 11 2026	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: White Clay Bicycle Club.
Saturday April 11 2026	Positive Strides Spring Classic Easton MD 13th Annual Spring Classic Bike Tour on April 11, 2026, in support of its mission to build confidence, self-esteem and a sense of accomplishment for children and adults with physical, cognitive and emotional challenges. 25, 50 or 62-mile ride along some of the most scenic routes in Talbot County. Sponsored by: Positive Strides Therapeutic Riding Center
Saturday May 2 2026	C3 Tri-County Ice Cream`Classic Easton MD “Chesapeake Cycling Club's premier springtime road cycling event on Maryland's Eastern Shore featuring fully-supported 100, 65, 36 and 23 mile routes.” Sponsored by: C3-Chesapeake Cycling Club
Sunday May 3 2026	Five Boro Bike Tour New York NY The TD Five Boro Bike Tour returns May 3, offering 40 miles of car-free streets through all five boroughs. Join 32,000 riders for this event before registration closes this Wednesday.The TD Five Boro Bike Tour returns May 3, offering 40 miles of car-free streets through all five boroughs. Join 32,000 riders for this event before registration closes this Wednesday. Sponsored by: Bike New York
Saturday May 9 2026	Six Pillars Century Cambridge MD Cycle the Scenic back roads of picturesque Blackwater Wildlife Refuge in Dorchester County, MD. Choice of three flat routes: 37 miles, the famous 56 – mile Ironman Eagleman course, or our beautiful 100 – mile century course that takes you through quaint townships along the Chesapeake Bay and back through serene woodlands.
Friday May 15 2026	Bike to Work Day DC, Maryland and Virginia Ride alone, with coworkers, or meet up with new friends in a group ride (convoy) led by more experienced bicyclists. Treat yourself! Register and participate to get your free Bike to Work Day T-shirt from your local pit stop on event day. There are over 100 of them across the DM‎V.
Saturday May 16th 2026	Tour de Chesapeake Mathews VA The 26th annual tour de chesapeake welcomes you to Mathews County, virginia. Celebrate the arrival of spring with a weekend of scenic cycling – great flat routes with views of the water everywhere you turn, delicious local eats, toe-tapping music, and nice, down-home folks to help you with whatever you need! Mathews County has just one traffic light in the entire county, and it’s on a drawbridge. Sponsored by: Mathews Outdoor Club
Saturday May 16 - Sunday May 17 2026	TO‎SR‎V Tour of the Scioto River Valley Yoctangee Park, Chillicothe, Ohio All routes begin and end at Yoctangee Park in Chillicothe, Ohio, creating a true home base for the entire weekend. Camp once, settle in, and enjoy two full days of riding, community, and celebration. The routes blend the best of the traditional TO‎SR‎V experience with new options that explore the roads, trails, and terrain surrounding Chillicothe. Riders can choose from rolling countryside, challenging hill routes, or a flat trail alternative along the Paint Creek Trail.
Wednesday, May 20 2026 at 7 pm	The Ride of Silence Washington DC On Wed. May 20th, 2026 at 7:00 PM, the Ride of Silence will traverse and unite the globe as nothing before it. Cyclists in 203 locations world-wide will take to the roads in a silent procession to honor cyclists who have been killed or injured while cycling on public roadways. Meet at Freedom Plaza, 1350 Pennsylvania Ave NW across from the Wilson Building. Ride past the Capitol to Navy Yard and end in front of the DD‎OT and US‎DO‎T HQs. Tentative route: https://ridewithgps.com/routes/50863678
Friday May 22- Monday May 25 2026	Chestertown Weekend May 22- 25 (Formerly known as the Kent County Spring Fling) Washington College, Chestertown MD Rides for all levels and abilities. Distances from 10 to 100 miles. Lodging at Washington College. The Chestertown Weekend is the closest thing I know of to the old Great Easter Rally and Cycle Across Maryland rallies of the 70s, 80s and 90s. Sponsored by: Baltimore Bicycle Club
Saturday May 23 2026	Tour de Madison Hoover Ridge, Madison VA 38th Annual Tour de Madison features metric century, intermediate, and family cycling routes through the Virginia countryside, benefiting local parks. Sponsored by: Blue Ridge Cyclery Events
Saturday June 6 2026	Tour de Talbot Easton MD Experience the Eastern Shore’s most scenic and historic region by bike. Three supported distances are available—30, 40, or 62.5 miles—all of which include at least two rest stops. Sponsored by: Talbot Thrive
Saturday June 13 2026	Patuxent Rural Legacy Ride Upper Marlboro, MD 22, 35, 44 or 64 miles through Prince George's County's Patuxent River area where Maryland's Rural Legacy Program is protecting farms, wetlands, and woods from development. Start from the picnic pavilion and group campground of the Patuxent River Park's Jug Bay Natural Area. Proceeds benefit Patuxent River Park, Merkle Wildlife Sanctuary and community projects in the Town of Eagle Harbor. There will be no on-site registration on the day of the ride. Limit 800 riders. Sponsored by: Oxon Hill Bicycle and Trail Club
Friday June 26 - Sunday June 28 2026	Bike Virginia Sunshine & Spokes Getaway Shepherdstown, Boonsboro, Harpers Ferry and Sharpsburg Bike Virginia returns this year as a three-day weekend centered on Shepherdstown, Boonsboro and Harpers Ferry Sponsored by: Bike Virginia
Saturday June 27 2026	Delaware Doublecross Metric Smyrna, DE 19977 A bicycle ride nearly anyone can do that crosses and “doublecrosses” Delaware in 62 total miles (metric century) over flat terrain. In addition to the traditional metric century route, ride either 31-mile loops for a shorter ride. Sponsored by: White Clay Bicycle Club
Saturday, June 27 2026	Bay to Bay Betterton, MD 21610 Four routes between 26 and 102 miles in length. The flat loop routes take in the scenery of the heartland of the Upper Eastern Shore of Maryland and Delaware including farmlands, old country homes, quaint towns, and great country stores. Sponsored by: Chestertown Lions
Tuesday July 21 - Saturday June 25 2026	Bon Ton Roulet Geneva NY Tour through the beautiful Finger Lakes region of New York State. Sponsored by: Auburn YM‎CA
Saturday July 25 2026	Spellbound Century Mount Holly, Burlington County, NJ Ride by local horse farms and historic towns on mostly flat roads and some challenging rolling hills. 20/45/63/100 Miles Sponsored by: Spellbound Community Giving Corp
Saturday July 25 - Sunday July 26 2026	Amishland and Lakes LaGrange, Indiana 46761 Amishland and Lakes bicycle tour visits a world where lifestyles have remained almost unchanged for over a hundred years. The 9 routes range from 22 to 100 miles, offering smooth, quiet roads, where buggies are numerous and cars are few. Sponsored by: Michiana Bicycle Association
Saturday August 1 2026	Mountain Mama Road Bike Challenge Monterey VA This yearly event features 2 States, 3 Counties, 9 mountains, 105 miles, and over 10,000 feet of climb. Six routes to chose from. Sponsored by: Highland County Recreation Commission
Saturday August 8 2026	Shorefire Century Middletown DE Ride beautiful, scenic routes (35, 65 and 100 miles) taking you through flat to gently rolling farmland in central Delaware as the route follows lesser traveled roads from Middletown to Clayton, Hartly, points south, and back Sponsored by: White Clay Bicycle Club
Sunday August 16 2026	Covered Bridge Classic Lancaster, PA The Covered Bridge Classic is a premier Pennsylvania ride now in its 47th year. It offers beautiful routes of 100 mile, 66 mile, 54 mile, 31 mile, and 17 mile routes, in Lancaster County. Each route traverses through covered bridges and passes Amish farms. All routes cover rolling terrain with moderate climbing. Sponsored by: Lancaster Bicycle Club
Saturday August 22 2026	Iron Furnace Fifty Snow Hill, MD 21863 All routes are flat, fast and fun. You'll be riding through the Great Pocomoke Forest and surrounding countryside on lightly-traveled rural roads. Three Options: 50K 50 Mile 100K Sponsored by: Furnace Town Foundation
Sunday, August 23 2026	Reston Century Reston, VA 3 routes: 31 mi \| 50 km; 62 mi \|100 km; 100 mi \| 162 km Sponsored by: Reston Bike Club
Sunday, August 23rd 2026	Brandywine Tour Kennett Square PA Brandywine Valley Tour featuring covered bridges, picturesque villages, and amazing vistas! Enjoy any of five gorgeous routes: 20, 35, 50, 60, & 100 miles Sponsored by: Delaware Valley Bicycle Club
Saturday August 29, 2026	Scratch N Denton Gravel Grinder 108 N 8th St, Denton, MD 21629 DelMarVa's First and Only Gravel Cycling Event! Three routes (all Mixed Gravel and Smooth Tarmac): 53.9 mi/403' elevation; 37.4 mi/294' elevation; 25.4 mi/190' elevation Sponsored by: Chesapeake Cycling Club
Saturday September 12 - Thursday September 17 2026	BR‎AT Bicycle Ride Across Tennessee David Crockett State Park, Lawrenceburg TN & Cedars of Lebanon State Park, Lebanon TN The Bicycle Ride Across Tennessee (BR‎AT) is a multi-day bicycle tour through a different part of Tennessee each year. Join us through small towns, farm country, and some of the best cycling Tennessee has to offer. Sponsored by: Tennessee State Parks. The ride benefits the development and protection of the Cumberland Trail, a 300-mile-long footpath down the eastern edge of the Cumberlands.
Saturday September 26 2026	50 States Ride Washington DC Bike every one of the 50 state streets in D.C. It’s an extravaganza of state streets, hills, tired legs, and wide smiles. Sponsored by: Washington Area Bicyclist Associataion (WA‎BA)
Saturday September 26 2026	Rolling Donuts ride Queen Anne's County 4-H Park, 100 Dulin Clark Road, Centreville, MD 21617 A sweet, late-season cycling event through the bucolic farmland and pastural countryside of Maryland's Eastern Shore. Flat, Fast and Fun! Sponsored by: Chesapeake Cycling Club
Saturday September 26 2026	Cycling for Our Heroes Havre De Grace, MD 21078 Routes of 27, 32, and 61 miles in Harford County, Maryland Sponsored by: Fisher House Foundation
Sunday September 27 2026	Official Wild Goose Chase Cambridge MD The Wild Goose Chase is a celebration of women’s cycling—and of the incredible Blackwater National Wildlife Refuge itself. Routes of 11, 19, 32, 50, and 64 miles. NO‎TE - This is a women's only event. Sponsored by: The Friends of Blackwater National Wildlife Refuge
Saturday October 3 - Saturday October 10 2026	Mountains to Coast Ride Mount Airy to Hatteras Island, NC The Cycle North Carolina Mountains to Coast Ride is a 7-day, fully supported bicycle tour traveling along scenic back roads that showcase rural North Carolina. The Mountains to Coast Ride is a point-to-point ride, not a loop ride. Sponsored by: North Carolina Amateur Sports
Sunday October 4 2026	Anne Arundel County Lifeline 100 Millersville, MD 21108 Scenic 65 and 100 mile county tours with water views and historic sites, 15 and 30 mile flat, paved trail rides Sponsored by: BikeAA‎A
Thursday October 22 – Sunday October 25 2026	Amelia Island Hub Tour Fernandina Beach, FL 32034 100-200 Miles. Choose the miles you want to ride each day. Registration fee covers three hotel nights at double occupancy, SA‎G, insurance, support, staff, maps, and most daily meals. Sponsored by: Bike Florida
Thursday November 5 - Sunday November 8	Florida Coast-to-Coast Bicycle Tour St. Petersburg, FL to Titusville, FL. All-ages, co-ed tour across the state of Florida. This tour begins in St Petersburg, and we ride our bikes over to Titusville (West to East). Once in Titusville, we board a bus back to St Petersburg. ~210 Miles Registration fee covers three hotel nights at double occupancy (single rooms are available for an extra fee during registration), SA‎G, insurance, support, staff, maps, a daily social gathering, and transportation from Titusville back to St. Pete. Sponsored by: Bike Florida
	-- No events posted for December --

To contact the club, please send email to:

contactohbike@gmail.com