Events: The 2026 Summer Event Calendar

For as long as any cyclist could remember, summer events vaporized in the eastern humidity. Summer events for cyclists meant races - a pause on the spring classics until teammates wanted to partake in fundraiser rides or wait until autumn. With the exploding popularity of gravel events, the summer fondo calendar has swelled, providing accessible events. 

Each listed ride is known for doing one particular thing well. Whether it’s a post-event party, cloaked in history, or a monolithic climb at the end, look for memorable parts to each outing. With the exception of one event, each route is considered gravel. Most events have a long and short course option. What matters most is the rise of the summer cycling event. Here’s to hoping for an eventful summer riding season.

Brandywine Valley Roubaix XI - Brandywine, PA - June 21

Located later in the season than normal, Brandywine Roubaix XI is one of most approachable events on the calendar. With two options: metric century and metric half century, Brandywine is in its eleventh year of exploring Chester County, PA, hills, dales, roads, and farmways. 

Steeped in colonial history, Brandywine is famous for its role in the American Revolution. The course is suitable for any bike with tires wider than 28mm. Slap some cyclocross tires on your road bike, pull your cross bike down from the rafters for some summer solstice fun, or roll the gravel bike to the start, this wallet-friendly event will explore some of the overlooked roads in southeastern Pennsylvania. With its approachable entry fee, course options, and historical rest areas, the Brandywine Roubaix XI is a great first-day-of-summer option.

North Winds Gravel Classic - Rodman, NY - July 11

A reader suggestion, the North Winds Gravel Classic, claims to showcase the fastest gravel in the Northeast. With gusts off of Lake Ontario, participants can sail up and over Tug Hill, and claim a scant 3,500 feet of climbing for the entire day on the long course. For most of the event, 75% to be precise, riders will be on unpaved roads, including a trip into Winona State Forest.

While the event explores unpaved roads, North Winds Gravel Classic has some serious chunk to its gravel. Expect ATV roads that are listed as vehicular throughways, though you likely won’t see many cars. Even though speed is highlighted for this event, don’t discount the cratered climbs at both 35 miles and 53 miles, respectively. If the gales of July off Lake Ontario turn dusty, it could be a challenging day out, just like you hoped. Whichever course is selected, the post-race party is sure to a great place to swap race stories.

Grinduro - Lock Haven, PA - July 18

Only in Pennsylvania can IPA gravel - that’s Incredible PA gravel - make sense. Think of it like the Champagne of Beers gravel, but better. Grinduro Pennsylvania is back with its segment racing claiming the ultimate ‘Party-to-Race-Ratio.’ The only eastern American location for Grinduro - Italy, Scotland, and California being the other global locations - the setting takes advantage of the challenging central Pennsylvania hillsides the commonwealth is becoming known for.

Boasting two distances, 79 and 42 miles, each course media consists of 65% unpaved surfaces. The long course offers four timed segments and 6,500 feet of climbing. The Grindurito features a respectable 3,500 feet of climbing. And Grinduro is a great prep ride for the autumn challenge that is UnPAved. Central Pennsylvania is quickly becoming a gravel playground for those interested in challenging courses. So, too, are the post-event parties making a weekend out of the event mandatory instead of the regular smash and grab approach.

Tour of the Catskills - Tannersville, NY - August 8

It would not be a summer cycling season without mentioning Anthem Tours’ 19th annual Tour of the Catskills held in Tannersville, NY. This is one of the few pavement-only summer options around, but it’s not without a challenge. We’ve circled the Catskills enough times to recognize their beauty for road riding, which has been in operation for eighteen editions. It’s those sneaky hollows that hide monster climbs, including the infamous Devil’s Kitchen climb, that keeps Catskills riding exciting.

Once a three-event cycling race supporting a time trial, criterium, and road race, the Tour of the Catskills is now a 75-mile fondo heavily supported by the mayor of Tannersville, NY. The course is decisively challenging. We often approach it as a quasi-race that starts at mile twenty. The opening distance into Palenville, NY, is a rocketing downhill start before entering a categorized climb and bucolic upstate New York countryside. It’s the final ten miles that leave riders hanging on for dear life. The Devil’s Kitchen climb, a 2.4-mile 10% average ascent is nothing like we’ve ever experienced. Whether it’s summited or walked, the ride’s conclusion is hosted by Last Chance Antiques and Cafe. 

D2R2 - Shelburne Falls, MA - August 22

The Deerfield Dirt-Road Randonnee, known simply as D2R2, tops our list as the longest ride for the summer. With possible routes up to 180 kilometers (110 miles) and 13,000 feet of climbing down to a family ride distance, the D2R2 has a challenge for everybody. Celebrating its 21st year, D2R2 has demonstrated staying power as a fundraiser for the Frankland Land Trust. 

As the figures suggest, the D2R2 is a massive undertaking for those opting into the original route of 180K. Starting at 6:00am, riders are given the whole day to navigate the constant up-and-down topography as well as the knowledge the finish line campsite will be waiting for them with bonfires and food. This isn’t just a ride, it’s an experience, though long course finishers may find themselves asleep right around the time the party gets started. As many of our friends who have finished D2R2 have bragged, completing the weekend is certainly a bragadocious accomplishment.

Bucks Gravel - Erwinna, PA - August 23

Back for its second year, Bucks Gravel (formerly Fools Classic) returns to explore the upper Bucks County roads in Pennsylvania. At eighty miles in length, Bucks Gravel tackles those pesky steep cobbled bergs our area is known for. Last year we used the road bike with Cadex Classics tires while others used full gravel set ups. To add to the consideration, road riders voiced their wish to have a gravel bike, while some gravel riders pined for their road bikes. The course possesses thirty percent gravel, but those rocky roads are the ones requiring the most attention.

In truth, bike selection comes down to the weather leading up to the event. If it’s dry like last year, the gravel will be dusty on the steep climbs. If it’s damp, the foliage will provide traction. In the end, Bucks Gravel gets us excited because it’s right out the office door (and over a couple of gravel climbs). With the event’s move to a more northerly area, newer roads have been tapped. For this longtime resident, many of the gravel roads to the north had never been ridden until last year’s Bucks Gravel. Once clear of the course, expect savory food at the finish as well as local brewery options while comparing ride statistics. This is one of those rides you have to participate in to believe.

Our summer list is always a work in progress. But then again, so is the summer cycling event season. Numerous events have highlighted their return to the calendar last year, hinting at doubtful returns for the year. This means bike events, no matter the season, continue to recuperate from the tumultuous post-pandemic years. 

Meanwhile, these events are several we’re considering for this year or next. Think of all the new roads to ride! And if you’re coming into town for Bucks Gravel, send us a message. We’d love to show you around.