Rides and Events Icon

Have a favorite place to ride or a favorite ride? Wanna share it? Let us know and we will include it in this section.


Come in to the store and learn some of the great places Maryland and the surrounding area has to offer. One of our staff members will be more then happy to offer their suggestions and offer you some resources in our store. To get started check out the listings below. Check back often as we continue to add to the list!

Check this page often for updated listings of all types of cycling events in and around our area. Rides require, at minimum, an appropriate bike in good working order, water, and a helmet. We suggest a spare tube, energy food, maybe a little cash in case we stop, and your biggest smile! Many rides are held subject to weather. It's a good idea to confirm dates, time and any specific requirements, too. We'll see you out there — and have fun!

Weekly Events

Day Start Time Description Location Phone


6:00 PM

***April 14, 2020***Beginner Road Ride - Join us for a 15 - 20 mile road ride. Pace will be 14 mph average. Perfect for the new road cyclist or those who enjoy a relaxed pace.

Crofton Bike Doctor


Thursday Evening

6:00 PM

*** March 12, 2020 ***Our Thursday night group ride will be at 6:00 PM. We will be riding for one to two hours as daylight allows. This ride is for road. Average speed is around 18mph.

Crofton Bike Doctor




2020 Dates Coming Soon Crofton Bike Doctor Casual Trail Ride - A moderately paced social no drop ride that is perfect for a fitness (FX) hybrid, dual sport or new road rider! Leaving from the WB&A Trail Parking lot (on Patuxent Road) The ride will start in the parking lot( Wheels down at 8am) traveling north to Odenton, once in Odenton the ride will turn around head back to the parking lot, congratulations you’ve just completed 7 miles. Once back rider can choose to end the ride or continue to the end of the WB&A trail at the Patuxent river. This option will add about 4.4 miles for a total of 11.4 miles. Requirements for the ride: 1. Helmet 2. Water ( Recommend 2 bottles) 3. Any riders under 18 must be accompanied by an adult for the entire ride

WB&A Trail Parking Lot


Classes and Clinics

Women's Basic Bike Class: We’ll teach you basic cycling techniques and road side repairs that will allow you to get the most out of your riding time. You'll learn some tips and tricks to increase the fun factor while you are out on your bike. There will also be a Q & A Session.

Mechanics 101 for the New Bike Owner: This is the ideal class for the new bike owner or for the person who just wants to know a little more about how their bike works. You'll learn how to fix a flat tire, basic road side repair, and basic bike maintenance. Class space is limited to ten students per session.

Mechanics 201 for Advanced Cyclists: This class will cover all the basics that are used to adjust your bike and keep it properly running. We will cover such topics as gear and brake adjustments and other items related to general maintenance. This class features a low teacher-to-student ratio. Class space is limited to eight students per session. 

Mechanics 301 for the Home Mechanic: Learn the Tips and Tricks from the Pro's. Mechanics 301 will deal with general installation of bicycle components. Such as headset installation, bottom bracket  installation. This class is limited to four students since it is very hands on. Course material will be customizable somewhat by the participants.  Group Discounts Available for three or more students. We also offer one on one classes as well as off-site classes please contact us for more information.

Triathlon 101: Learn tips and tricks in preparing and participating in your first triathlon. Our Triathlon experts will help you prepare for your first triathlon and give you valuable information on how to avoid some basic mistakes. You'll know more of what to expect during your triathlon and be more prepared when race day arrives. Space is limited please RSVP.

Introduction to Bicycle Fit and Rider Comfort:  Learn how your cycling position affects comfort. We'll cover basic fit issues and solutions to address them.  You'll gain knowledge on how the three contact points affect your comfort and how to alleviate problem areas on your bike while increasing your understanding of the causes.

New Owners Bike Clinic

This is the ideal class for the new bike owner or for the person who just wants to know a little more about how their bike works. You'll learn how to fix a flat tire, basic road side repair, and basic bike maintenance. 

New Owners Clinics are generally held on Saturday's, with an occasional weeknight class. Class length is approximately an hour.

Have a group that is interested in learning more? Ask us about an on-site presentation to your group.

Day Start Time Description Location Phone

Saturday Sept 1st

9:00 AM

Ever wanted to know how to fix a flat? Some tips and tricks to help you get back on the road when something unexpected comes up?

Crofton Bike Doctor


Saturday Annapolis Bicycle Club Weekday Rides

Saturday Rides - Meet at the Davidsonville Park n Ride at Route 424 and Route 50. Ride varies by week, Deale, Galesville and Southern Anne Arundel County.


Date Event Name Location Description Phone

Apr 19, 2020

Nautica South Beach Triathlon

South Beach, FL

International Distance and a Classic Distance. The triathlon is held on the tropical shores of South Beach and hosting nearly 3,000 athletes as they swim, bike, and run through picturesque Miami Beach! The race features the International Distance, a .93 mile swim, a 24.25 mile bike and a 6.2 mile run; or the Classic Distance features a .5-mile swim, 20.7-mile bike and 4-mile run.

Apr 24, 2020

Ocean to Bay Bike Tour

Bethany Beach, DE

All routes start and end in Bethany Beach. Choose from a 30-, 50-mile, Metric Century & Century route. Completion of the ride is optional. Sag Wagon support available from 7:00 a.m. to 4:00 p.m. Designated rest stops with restrooms, light snacks & beverages. Continue the Tour After Party: from 11 a.m. to 5 p.m. (music, food vendors, door prizes, and more!) The ride will take place rain or shine.

Apr 24, 2020

Coastal Ride (2-Days)

Edenton, NC

The Cycle North Carolina Coastal Ride offers participants and their families a fun-filled 3-day weekend while both on and off the bike. Start your day by hopping on your bike and exploring one of the many fully supported routes this ride has to offer. Each day will feature a variety of routes ranging anywhere from 5 miles to 100 miles. The flat roads and minimal traffic counts will allow you to fully experience all of the sights and sounds of the Edenton area including an abundance of coastal wildlife and many historic sites that are deeply rooted to the local communities.

Apr 25, 2020

Rumpus In Bumpass

Lake Anna, VA

Hosted in the renovated Lake Anna Beach Marina, this race and venue are amazing. The swim lakes place in the southeast portion of Lake Anna, about 1/4 mile from where the “hot side” of Lake Anna empties into the cold side, resulting in water temperatures that are 4-6 degree’s warmer than the rest of the lake at this time of year. So, you can look forward to water temperatures in the mid 60’s The first open water swim event of the season starts out with a 9AM start so you can sleep in a little and maybe even bring the kids! The race site is unique because the transition area and finish line are surrounded by water on 3 sides with a view of the Blue Ridge Mountains to the West. Be sure to register early as we expect the return of this event to be extremely popular.

Apr 25, 2020

End Hunger Ride

Calvert Cty, MD

Join us for a day of biking along the western shore of the Chesapeake Bay. Pedal along the bay-front, marina, farmland and wineries while you enjoy the company of friends who share your same passion for biking. This is a fully supported event with routes ranging from 16 miles to a metric century. Whether you are a seasoned rider or just getting started, we have a route for everyone! Routes 16 miles to 63 miles.

Apr 26, 2020

Draw for Sight Bicycle Poker Run

Kent County, Maryland

***ESTIMATED DATE BASED ON PREVIOUS YEARS*** The Chestertown Lions Club welcomes cyclists to Draw For Sight Bicycle Poker Run Ride. The tour consists of a 36 or 60 mile rolling to flat course. The route 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.

May 2, 2020

Ride for the Feast

Ocean City to Balt City

The ride began in 2003 and has become one of the largest sources of funding for Moveable Feast. Riders and crew return year after year to be involved in this event because of the amazing people involved and for knowing they are making a difference in the lives of the clients of Moveable Feast. This is a 2 day event.

May 2, 2020

Six Pillars Century

Great Marsh Park Somerset Avenue Cambridge, MD 21613

***Registration is OPEN**** Blackwater National Wildlife Refuge near Cambridge, MD. The cycling event will include four ride choices, including a 37-mile fun and fitness ride, a 56-mile Ironman Eagleman 70.3 Course, and a 100-mile Century Course. Registration is open on Active.com


May 9, 2020

Capital 2 Capital Ride

Williamsburg/Richmond, VA

Always a customer favorite! Quarter, Half and Full Century Routes.

May 9, 2020

Iron Furnace Fifty

Furnace Town, MD

The 10th annual 50 mile ride that goes around amazingly beautiful Furnace Town on the Eastern Shore.

May 17, 2020

Gran Fondo New York

New York, New York

Join thousands of cyclists on a challenging 100 mile Gran Fondo and 65 mile non competitive Medio Fondo from New York City to Bear Mountain and back in an experience fit for a pro and open to anyone who loves to ride.

May 22, 2020

Kent County Spring Fling

Chestertown, MD

Come and enjoy four days cycling the lightly traveled roads of Maryland’s Chesapeake Bay Eastern Shore. Rides of 11 to 100 miles meander along flat to rolling roads — through rural towns and along scenic rivers.

May 30, 2020

Air Force Cycling Classic

Crystal City, VA

The Air Force Cycling Challenge Crystal Ride is an amateur, non-competitive, participatory ride, open to cyclists of all abilities. General entrants will start and end in Crystal City. The ride will be held on a closed circuit in and around the Pentagon, Crystal City and the Air Force Memorial. Participants can be challenged for up to 8 laps (100km) in 3.5 hours, either as a Standard Registrant, Corporate Challenge Team or as part of Team Sabre fundraisers.

Jun 5, 2020

Bike Travel Weekend


Join thousands of people throughout the world and go on a one- or two-night bike adventure during the weekend of June 5 - 7th, 2020 Camp or stay at a hotel, hostel, or friend’s house. Go solo, with friends, or a big group, and ride as many miles as you’d like. Just make sure the adventure you choose is your speed and you have a smile on your face at the end of the weekend.

Jun 13, 2020

Bike MS: Chesapeake Challenge

Easton, MD

A two-day 150 mile event, hosted in Easton, MD.

Jun 14, 2020

IronMan 70.3 Eagleman Triathlon

Cambridge, MD

A race steeped in triathlon history, held in a unique Chesapeake town on the Eastern Shore.

Jun 19, 2020

Bike VA (5 days)


The Bike Virginia Tour is pleased to partner with the Farmville-Prince Edward County Virginia region for the 2020 Bike Virginia Tour, the 33rd year of the annual cycling event. Farmville last hosted the event in 1997, and previously for the very first year of the tour in 1988.

Jun 28, 2020

Bay to Bay Ride

Maryland's Eastern Shore

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 27 and 104 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 27 mile ride goes through historic Chestertown for those who want a less challenging ride.

Jul 11, 2020

The Great Bicycle Tour - C&O Canal

Cumberland, MD

About A fully supported four-day ride on the C&O Canal. Join us as we begin in Cumberland, MD and ride to Mile Marker 0 in Washington, DC. 184.5 miles of no hills, no headwinds and no cars. Plenty of food, lots of support, ride at your own pace, well organized.

Jul 25, 2020

Wilderness 101

State College, PA

The Wilderness 101 is an ultra endurance 101 mile backcountry mountain bike race. The course is one super big loop composed of some of the best off-road riding central PA has to offer in the Rothrock and Bald Eagle State Forests.

Aug 1, 2020

Penn State Chocolate Tour

Hershey, PA

Routes of 10 miles to 100 miles. Funds raised at the annual Chocolate Tour support cancer research at the region's only comprehensive Cancer Institute committed to fighting cancer to find the cure

Aug 7, 2020

Mountain RIde (2-Days)

Brevard, NC

The Cycle North Carolina Mountain Ride is a perfect weekend getaway for any outdoor enthusiast and their families. The ride is a 2-day cycling festival featuring a variety of route options each day that focus on showcasing the beautiful landscapes that Western North Carolina has to offer. The routes vary from 15 to 70 miles and meader along rivers and streams through the Blue Ridge Mountains.

Aug 16, 2020

Covered Bridge Classic

Lancaster Campus of Harrisburg Area Community College.

Year after year our customers rave about the Covered Bridge Metric Century. Enjoy the scenery and covered bridges that Lancaster County Pennsylvania offers. The Lancaster Covered Bridge Classic (formerly the Covered Bridge Metric Century) is a classic Pennsylvania ride now in its 41st year. It offers beautiful routes of 100 miles, 65 miles, 33 miles, and 16 miles, covering some of the most scenic cycling terrain anywhere. Each route traverses through covered bridges and past Amish farms.

Sep 6, 2020

Shenandoah Mountain 100

Stokesville, VA

An ultra-endurance mountain bike race through some great trails and fire roads in the mountains of Virginia.

Sep 12, 2020

Civil War Century

Thurmont, MD

Beautiful ride through back roads in scenic, hilly western Maryland and southern Pennsylvania. The full century visits the Antietam, Gettysburg and South Mountain battlefield historical sites, with lots of climbing and descending along the way. One of the area's premier century rides, with great support and organization. Registration opens early June.

Sep 12, 2020

Fool's Gold MTB Race 50 and 100 miles

Dahlonega, GA

Fool's Gold 100 is part of the National Ultra Endurance Series and all governing rules of the NUE apply to the Fool's Gold 100. The 2016 Fool's Gold 50/100 will again be based out of the beautiful Montaluce Winery in Dahlonega, GA. As far as the course, expect lots of fast & flowy singletrack, some doubletrack, and a fair dose of gravel road grunts. There are a couple of longer sustained climbs, but the rollers will probably be the ones to get you.

Sep 12, 2020

Amish Country Bike Tour

411 Legislative Ave, Dover, DE 19901

Join us for the 34th Annual Amish Country Bike Tour on September 12, 2020!! Routes are 15, 25, 50, 62 or 100 miles through peaceful, flat(!), low-traffic Amish countryside. The 2019 routes are available at: https://ridewithgps.com/events/102159-amish-country-bike-tour. (we expect the course to be similar in 2020) Super early-bird rate of $35 per person will be available until December 31, 2019.

Sep 20, 2020

Three Creek Century

Newville, PA

Join us for a scenic bike tour through Cumberland County in Central Pennsylvania sponsored by the Harrisburg Bicycle Club. Featuring five ride distance options and homemade soup! Tour Cumberland County’s scenic countryside alongside the Yellow Breeches, Conodoguinet and Big Spring Creeks.

Sep 26, 2020

Cannonball Century

Curtis Memorial Park at 58 Jesse Curtis Lane Hartwood, Virginia

32 - 100 mile routes. The sprawling countryside of Stafford and Fauquier counties near Fredericksburg provides the ideal site for a fun, safe day of recreational bicycling. Secluded woodland roads, ranches and farms form the backdrop for Fredericksburg Cyclist's 20th annual Cannonball Century. Plan for a longer visit to include historic downtown Fredericksburg with craft & antique shops, unique family-owned restaurants as well as civil war era attractions, recognizing a pivotal time in our Nation's history.

Sep 26, 2020

Intercourse Amish Bike Ride

3730 Old Philadelphia Pike, Gordonville, PA 17529

The Intercourse Amish Bike Ride winds through rolling farmland on quiet, country roads. Forget the tourist traps, we'll take you on roads only the locals know, and refuel you with rest stops that continue our authentic Lancaster County feel. Choose from an 8-mile ramble ride, a 30-mile, and a 54-mile route. Post-ride, we'll gather for a time-honored Lancaster County tradition - a chicken barbecue in the park. Your post-ride meal, as well as pre-ride coffee and donuts, are included in your registration fee.

(717) 929-0327

Sep 26, 2020

Bike Your Park Day


Explore parks and public lands by bicycle on September 26, 2020 with thousands of others throughout the world on the same day. Ride any distance on roads, paved bike paths, or single track. Make a day of it and stop to enjoy a spectacular view, treat yourself to your favorite ice cream, cool your toes in a lake, or learn something new at an historical site.

Sep 29, 2020

NJ Mountain Bike Festival

Ringwood, NJ 08844

The festival is at Shepherd Lake Recreation Area in Ringwood State Park. A $5 parking fee per event vehicle will be collected by park staff. There is an additional $20 per adult entrance fee or $10 in advance. Kids are free.

(973) 506-9293

Oct 3, 2020

Mountains to Coast (7-Days)

North Carolina - Route Announcement in late January

Oct 3, 2020

Savage Century

Newark, DE

Enjoy the lovely state of Delaware while you ride various routes from 40, 60, 75 or 100 miles in the Savage century.

Oct 4, 2020

Lifeline 100

Kinder Farm Park

Earlybird 2020 Registration is Open! The Lifeline100 at Kinder Farm Park in Millersville, MD offers a unique organized ride experience for cyclists of all ages and abilities with scenic 100 and 65 mile routes on road and paved trail; and 30 and 15 mile routes on paved trail only. Thanks to our generous sponsor Prophasys, riders with special needs and their accompanying rider can register at a special 2 for 1 rate.

Oct 10, 2020

Seagull Century

Salisbury University Salisbury, MD

Seagull Century is a cycling tradition in the mid Atlantic area. Don't miss one of the Top 10 Centuries in North America.


Oct 11, 2020

Covered Bridges Ride

Tinicum Park

You have five great routes to choose from -- the family-friendly 20 and 34 mile routes (both use the towpath along the Delaware river, which is a fine-cinder and hardpacked dirt trail, for part of these routes), or the hillier 35, 50 or 63 mile rides (all on paved roads) -- plus plenty of great food. Travel through up to six historic covered bridges. Fatter tired bikes work best on the cinder-based paths for the 20 and 34 mile routes, which visit one (20) or two (34) bridges. All rides conclude with a Grande Finale Picnic.

Oct 24, 2020

Dirty Dozen

Pittsburgh, PA

The 38th Annual Dirty Dozen Bicycle Ride up 13 of the Pittsburgh area's steepest hills

Nov 7, 2020

The Cider Ride

Dance Place, 3225 8th St NE

This ride will take you through the woods on Maryland’s beautiful trails —a whole new world, accessible by bike, and right in your backyard! Three route choices mean you can ride for 10, 30, or 55 miles, enjoying fall-themed treats at pit stops along the way.

Nov 7, 2020

2019 Gravel Gobbler

174 Middle Road, Nassau, NY 12123

Join the Mohawk Hudson Cycling Club for its second annual Gravel Gobbler ride on Saturday, November 7, to benefit the Regional Food Bank of Northeastern New York. With two gravel rides of 23 and 38 miles, plus a road route of 31 miles, you’re sure to find the perfect loop. Pedal through the rolling countryside around Nassau, New York, and cruise quiet roads past farms, scenic vistas and country estates.

(518) 708-3762

Nov 8, 2020

Cranksgiving 2020

Crofton Bike Doctor

Cranksgiving is a food drive and a bike ride all wrapped into one. Ride your bike and help those in need over the holidays enjoy a meal or two. First hosted in New York City in 1999 by a group of bicycle messengers. There are events all over the county. This is a family friendly event.