Kickin’ Annual Cycling Rides Throughout Maryland

Century and metric bike rides are back! Geared for every level.

This is serious fun if you enjoy cycling. And if you’re just getting back into it, planning to do these rides is great incentive to get on the seat every week.

New to Annual Cycling Rides?

Eastern Shore rides are flat. The biggest “hill” is a highway overpass. Western Shore has rolling hills. Hard-core and some elevation? Look for rides in northern Maryland’s hills of Civil War territory.

These rides are all fundraisers and they have a fee. But that means they’ll be watching out for you with people available to repair bikes or pick you up in emergencies. Usually, they’ll have rest stops with energy snacks and water. It’s cheaper the earlier you register. I’ve waited until day of to register because I wanted to check the weather first, but be aware than some don’t allow that. Check the rules.


Positive Stride Annual Bike Ride through Talbot County, MD

Positive Strides Spring Classic

Easton, Maryland

Cost: $55 – price increases after April 15

Difficulty: Easy – depending on length

Ease into the cycling season with this one. Cyclists start in Easton and can participate in a 25, 50 or 62-mile ride along some of the most scenic, and very flat, routes in Talbot County on Maryland’s Eastern Shore. There are three fully supported rest stops and a light lunch at the end of the ride. The event will take place rain or shine.


End Hunger Bike Ride out of Huntington, MD
Courtesy End Hunger Facebook Page

End Hunger Bike Ride

Huntingtown, Maryland

Cost: $39-$49

Difficulty: Easy – depending on length

Enjoy a day of cycling along the western shore of the Chesapeake Bay along the bay-front, marina, farmland and wineries. This is a fully supported event with routes ranging from 16 miles to a metric century, including a 16 mile New Rider route. Food and live music provided at the end of the ride. New this year, individual yoga stretching session and an afternoon yoga class once you finish your ride!


Courtesy Bethany-Fenwick Area Chamber of Commerce Facebook Page

Ocean to Bay Bike Tour

Bethany Beach, Delaware

Cost: $65 – $75, no day-of registration

Difficulty: Easy – depending on length

This is a popular one going from Delaware’s Atlantic Ocean shores to Delaware Bay. More than 2,500 cyclists of all levels tour through Sussex County’s beautiful beaches, bays, and farmland with 30-, 50-, metric century, and century rides on flat terrain


Bikes & Beer bicycle ride with Flying Dog Brewery out of Frederick, Maryland
Courtesy Flying Dog Brewery

Bikes and Beers with Flying Dog Brewery

Frederick, Maryland

Cost: $40 to $70 on day of ride

Difficulty: Moderate to Difficult

Part of a series of Bikes and Beers rides, this one out of Frederick features a 15, 30, and 50-Mile ride departing from Flying Dog Brewery and travels through rolling hills. Pre Ride: Free High Brew Coffee and pastries to get you fueled up. Local bike shops will offer free last minute tune-ups! All rides will feature rest stops with refreshments and will finish up back at Flying Dog. All riding levels welcome. Post Ride festival at Flying Dog featuring: a Pint Glass for every rider, as well as koozies, two beers, live music and food trucks.

May 1

Courtesy Six Pillars Century Facebook Page

Six Pillars Century Blackwater Tour

Cambridge, Maryland

Cost: $65, $70 in March – increases closer to ride

Difficulty: Easy – depending on length

The ride starts at the Great Marsh Park in historic Cambridge. You’ll cycle the majority of this ride through the beautiful and picturesque Blackwater Wildlife Refuge in Dorchester County. There’s a choice of three flat routes: 37 miles, the famous 56-mile Ironman Eagleman course or the 100-mile century course through quaint townships along the Chesapeake Bay and back through serene woodlands.  Along the course are fully stocked rest stops crewed by friendly and helpful volunteers. Upon your return, you are treated to a picnic in the park.

May 7, 2022

“Tree Nuts” from 2019. Courtesy Baltimore Kinetic Sculpture Race

Baltimore Kinetic Sculpture Race


Cost: Free

Difficulty: Not

Kinetic Sculptures are amphibious, human powered works of art custom built for the race. Each May, the American Visionary Art Museum (AVAM) produces and hosts the East Coast Kinetic Sculpture Race Championship on the shore of Baltimore’s Harbor in central Maryland.  The eight-hour race covers 15 miles—mostly on pavement, but also including a trip into the Chesapeake Bay and through mud and sand. The rest of us cycle behind the sculptures as they traverse the route and complete the obstacle courses. It a fun, rolling party. Wearing costumes is encouraged.

NOTE: due to COVID, this ride doesn’t resume until next year.

May 8 & 22

Courtesy Maryland Endurance Challenge

Maryland Endurance Challenge

Near Frederick, Maryland

Cost: $40, up to $90 on day of

Difficulty: Created to be Very Difficult

This is for experienced riders ONLY.

The idea is to peddle up and down big hills until you’ve climbed as much elevation as Japan’s Mt. Fuji, Alaksa’s Denali or — if you’re really hard-core — Mt. Everest.

There are two parts to the ride:

Part 1 – Climb to the the Clouds (May 17) – The 1.7 mile climb will ascend Catoctin Mountain through beautiful Gambrill State Park, topping out at 1,600 feet above sea level. Riders then go down the same route you climbed.

Part 2 – Freestate & Mason Dixon (May 20) – This is a timed event where cyclists wear chips and ride for speed. It features 3, 6, or 12 hour rides. And they ride in the afternoon, ending by 8pm. Riders begin & end at Mount St. Mary’s University in Emmitsburg, Maryland. More than 200 riders gave it a go last year.

June TBA

Courtesy Southern Maryland Electric Cooperative Facebook Page

Southern Maryland Electric Cooperative 75

Hughesville, Maryland

Cost: $40 – $60
Difficulty: Moderate – some rolling hills

This is a 29, 47 or 75 mile ride through rural Western Shore, south of Washington, DC. You’ll travel through the byways of southern Maryland to Colton’s Point on the shores of the Potomac River and along portions of the scenic Three Notch Trail. At the finish line, enjoy a sub sandwich, cold beverage and summertime music.

June 13

Courtesy Oxon Hill Bicycle & Trail Club Facebook Page

Patuxent River Rural Legacy Bike Ride

Upper Marlboro, Maryland

Cost: $30 – $50 close to ride day
Difficulty: Moderate (some rolling hills)

This ride is about the countryside. You’ll roll through Prince George’s County’s Patuxent River area where farms, wetlands and woods are being protected from development with Maryland’s Rural Legacy Program. There will be scenic routes of 22, 35, 44 and 64 miles on paved, country roads.

June 19

Courtesy Union Craft Brewing

Bikes and Beers with Union Craft Brewing

Baltimore, Maryland

Cost: $40 – $70 close to ride day / Party only: $25
Difficulty: Moderate (some hills)

Union Craft Brewing hosts this 15, 30 and 50-mile ride through scenic Baltimore. The historic city has bike trails in parks and parkways snaking throughout the city, with some routes along historic neighborhood streets.

Local bike shops will offer free last minute tuneups at the starting point, and all rides will feature rest stops with refreshments. You’ll end up at Union Craft for a post-ride festival with live music, food trucks and Union Craft beer. Each rider gets a pint glass for the tasing and two beers of your choice.

June 27

Courtesy Chestertown Lions Club

Bay to Bay Ride

Betterton, Maryland

Cost: $25 – $40 close to ride (registration close June 8)

Difficulty: Moderate (some rolling steep hills)

On the fourth Sunday of June each year, the Chestertown Lions Club welcomes cyclists to its summer bicycling challenge, the Bay to Bay ride. The tour consists of five 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. The 26-mile ride goes through historic Chestertown for those who want a less challenging ride.

July 17

Courtesy Pauline F. & W. David Robbins Family YMCA

Heart of the Chesapeake Bike Tour

Cambridge, Maryland

Cost: $60

Difficulty: Easy (depending on length)

You choose from the Metric Century (66 miles), Half Century (52 miles), Ragged Point Ride (32 miles). Ride down a peninsula with the Choptank River on one side and the Chesapeake Bay on the other. The metric rides go through the countryside, past Harriet Tubman Underground Railroad Museum and through Blackwater National Wildlife Refuge and through the historic town of Vienna on the Nanticoke River.

July 30

Courtesy Bike to Beach Ride for Autism

Bike to the Beach

Washington, DC & Baltimore, MD

Cost: $40-$500 depending on which level you choose

Difficulty: Moderate (long ride)

This is a unique 100 mile ride. There are no shorter routes. And it’s one way. Registration is limited and it fills up.

Groups start in Washington, DC and Baltimore, Maryland. They converge near Annapolis, where cyclists put their bike in a truck and hop on a bus for a ride across the Bay Bridge to the other side of the Chesapeake Bay. Then, they get back on the bikes and ride down country highways to Dewey Beach, Delaware.

After the post party there, riders board buses and again and return to either Washington or Baltimore.

August 28

Courtesy Iron Furnace Fifty

Iron Furnace Fifty

Snow Hill, Maryland

Cost: $46 – $70
Difficulty: Easy – depending on length

The Iron Furnace Fifty is an annual Spring bike ride through the beautiful rural Lower Eastern Shore of Maryland organized by the Rotary Club of Snow Hill and Furnace Town Living Heritage Village. There are 50K, 50 Mile, and 100K routes on rural Maryland roads among woods and farms. All routes begin and end at Furnace Town.

All routes are flat. You’ll be riding through the Great Pocomoke Forest and surrounding countryside on lightly traveled rural roads.

In addition to the enjoying the natural beauty of the Pocomoke Forest, riders are provided free ice cream from a working dairy at one of the rest stops. Lunch and drinks are provided at the end of the ride at the Furnace Town picnic pavilion.

September 11

The Civil War Century

Thurmont, Maryland

Cost: TBD (limited to 1,600 riders & is always sold out)

Difficulty: Difficult (lots of elevation)

Bicycling Magazine featured the Civil War Century in it’s Fun 100s (View the Article). Baltimore Magazine named the Civil War Century as the ‘Best of Baltimore” Bike Ride (Read the Write Up). All children under 18 must be accompanied at the event by a responsible adult. The Civil War Century is an event with five different routes that are designed for different ability levels and are described below. The 25 mile Covered Bridge Quarter Century for beginners and those that don’t ride long and hilly rides up to the 100+ mile Civil War Century which is intended for experienced, well trained cyclists that have done at least a couple of centuries already. For the history buff, you can visit Crampton’s Gap, South Mountain, Antietam and/or Gettysburg battlefield sites. You’ll see all four if you elect to ride the full century.

September 16

“You may not associate Maryland with climbs, but Gran Fondo Maryland has one of the highest ratios of elevation gain per mile of any Gran Fondo National Series event. But don’t worry, the perfect roads and cooler early fall temperatures make this one of our most popular events.” – Gran Fondo Facebook Page

Gran Fondo Ride

Frederick, Maryland

Cost: Price goes up closer to ride. On day of – $120-$175 depending on length

Difficulty: Difficult (created to be challenging)

Part of a series of Fondo rides in U.S. Three routes of various lengths & elevation… but elevation is the key word Just 50 miles from either Washington, D.C. or Baltimore, the town of Frederick, Maryland is surrounded by some of the best cycling roads in the United States. Riders can come race the timed sections and cruise along with your friends along a course that travels through state parks, municipal forests, protected watersheds, and the Catoctin Mountain National Park. After exploring this incredible region, riders will return back into historic downtown Frederick and enjoy finish line festivities including a raffle and a gourmet lunch from renowned chef Bryan Voltaggio!

September 19

Courtesy Shore Rivers Facebook Page

Ride for Clean Rivers

Wye Mills, Maryland

Cost: TBD

Difficulty: Easy-Moderate (generally flat)

Ride the beautiful back roads of Talbot and Queen Anne’s Counties in support of clean water for our Mid-shore rivers.  Riders of all ages and levels enjoy cycling across the beautiful Eastern Shore of Maryland. Chesapeake College, Wye Mills, MD.  Choose from 20-mile, 35-mile, or 62-mile (metric century) routes. All rides include SAG support and rest stops with food and drink. Party to follow.

September 25

Courtesy DC Bike Ride Facebook Page

DC Bike Ride

Washington, DC

Cost: Early registration – $62. With jersey – $119.

Difficulty: Easy-Moderate (generally flat)

This is a great way to see Washington, DC. The 20-mile ride is completely car free and goes past the monuments and historic sites of the nation’s capitol city. It has fully stocked rest stops with sanitizing stations, water and fresh produce. Also extensive mechanical support along the way. The ride finishes in a festival in front of the U.S. Capitol. Don’t have a bike yet? They offer on-site rentals.

October 3

Courtesy Anne Arundel County Lifeline 100 Century Ride Facebook Page

Lifeline 100 Century Ride

Kinder Farm Park, Millersville, Maryland

Cost: TBD

Difficulty: Easy – Difficult

These routes wind throughout scenic Anne Arundel County including views of downtown Annapolis, the Severn River, southern Anne Arundel County, BWI/Marshall airport and more! The full century ride includes 4 supported rest stops.  The metric century or approximately 65 mile ride includes 3 supported rest stops.  The 30 mile ride includes 2 supported rest stop. The 15 mile ride includes 1 supported rest stop. The 30 and 15 mile rides are on paved trails.

October 9

Sea Gull Century Bike Through Maryland
Courtesy of Sea Gull Century Facebook Page

Seagull Century

Salisbury, Maryland

Cost: $75 (limited to 4,000 riders & can fill up)

Difficulty: Moderate – Difficult

Sea Gull Century, a nationally acclaimed bicycling event, is the grande finale of the Maryland cycling season. It begins and ends on the campus of Salisbury University, touring the picturesque Eastern Shore of Maryland and offers two routes: 100 miles to Assateague State Park (on the Atlantic Ocean, where horses run wild) or 65 miles to Cyress Park.

If we missed any, please let us know in the comments below.


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