Frederick County, Maryland, is home to a vast and versatile range of awesome endeavors. From acclaimed attractions to be enjoyed year-round, to select seasonal offerings that draw in locals and visitors alike, the options are seemingly endless.
Regarding the previously mentioned seasonal offerings, you have an abundance of beloved festivals, fairs, races, and other events to take in throughout the county, occurring at various times throughout the year. Here are eight great can’t-miss examples of the most hopping happenings to check out in Frederick County, Maryland.
Sailing Through the Winter Solstice
Since 2016, the scene at Carroll Creek Park has been dazzling residents and drawing in visitors to Downtown Frederick even in the coldest of months. That’s because the aptly named Sailing Through the Winter Solstice is a heart-warming, wowing spectacle to behold—a true treat to take the edge off the bitter cold and a viable reason for bracing frigid conditions and getting outdoors.
Made possible by the nonprofit organization Color On The Creek, Sailing Through the Winter Solstice features a versatile themed display of lighted, decorated sailboats, set up along Carroll Creek. The boats can be viewed any time, day or night, November through March, although coming at night when all are illuminated is especially enthralling and nothing less than magical, to say the least.
In addition to serving as a delightful diversion to the chilly weather, Sailing Through the Winter Solstice operates as a fundraiser for nonprofit organizations throughout Frederick County. Learn more about this event and all others made possible by Color On The Creek via their website at www.coloronthecreek.com.
Fire in Ice
In addition to the aforementioned, folks in Frederick have another cold-weather endeavor to celebrate. It’s the annually presented Fire In Ice festival. Made possible by the Downtown Frederick Partnership, it’s been a steady mainstay tradition for many years now, serving to keep the spirits of locals and visitors alike warm and cheerful. It rightfully comes as a most befitting, mood-boosting midwinter endeavor, during that lean season right after the holidays when you feel like springtime is still too far off!
The highlight of the event is, of course, the hundreds of ice sculptures gracing the Downtown Frederick area. But there’s plenty to be said about the featured entertainment as well, including live ice carving demos, and frozen featured activities like playing ice golf or checking out an ice bar!
The fire component in the festival’s name can be summed up by the presentations of professional pyrotechnic performers. Their goal is to delight and amaze onlookers with breathtaking, masterful feats involving fire and flame.
The next Fire in Ice will take place from January 31 through February 2, 2026. You can learn more about the upcoming 2026 event on the Downtown Frederick Partnership’s website.
Maple Syrup Festival
Arguably the grandest of all maple sugaring events throughout the state, the annually presented Maple Syrup Festival at Cunningham Falls State Park in Thurmont is a tradition that has been running strong and constant for well over five decades. Always held two consecutive weekends in March, the festival primarily strives to highlight the history behind maple syrup making in Maryland.
Attending guests have an array of activities and exciting endeavors to explore throughout the festival’s run. Such offerings include witnessing the onsite maple syrup making process in action, taking hayrides through the resident maple grove, participating in a “flipped” out pancake race (where you try to flip a pancake while running ahead of other contestants), and so much more.
Because breakfast is the most important meal of the day, and maple syrup is such an essential part of so many breakfasts, you can count on a featured feast of locally made breakfast items to be available for purchase. Some are more traditional, while others take creative liberties as unique, one-of-a-kind “maple-syrupy” concoctions you can’t pass up.
The Maple Syrup Festival is hosted by the Friends of Cunningham Falls State Park and Gambrill State Park at the William Houck Area of Cunningham Falls State Park. A $5 per person donation fee is requested upon entrance. Learn more about the festival and all details on the upcoming 2026 installment as they become available at www.friendsofcunninghampark.org.
Maryland Iron Festival
Hosted annually by none other than the Catoctin Furnace Historical Society, this free-for-all two-day festival draws in visitors from all over Maryland and surrounding states throughout the Mid-Atlantic region. It serves the joint purpose of honoring Frederick County’s historic role in iron production, specifically, as well as the area’s overall history and heritage.
As a springtime festival, it packs a plethora of events to keep crowds buzzing all weekend long. Do you like live music and entertainment? Well, they certainly have a versatile line of musicians to keep the beat at any event. Then there are all those bountiful vendors to boot, all featured via the onsite Makers Market. Other delightful offerings to check out include guided garden and trail tours around the historic furnace site, plein air art shows, kid-friendly activities, delectable food and beverage offerings, talks by expert historians and archeologists, and arguably their most popular featured event—onsite blacksmithing demonstrations featuring live iron pouring!
The next installment of the Maryland Iron Festival will take place on May 16 and 17, 2026. Again, it will be held on location at the Historic Catoctin Furnace at 12610 Catoctin Furnace Road, Thurmont, Maryland 21788. Learn more on the website at www.catoctinfurnace.org.
In The Streets
This is a fun, free-to-attend, ongoing annual festival celebration that has been going strong for over 40 years and remains as popular as ever! A tradition started back in 1983, the idea behind In the Streets came about following a major renovation to the town, which had forced the closure of Market Street for several months. The festival was then-Mayor Ron Young’s answer to getting folks to come back out and enjoy a major street party in the aftermath of all the construction. Serving to encourage and uplift new and existing commerce alike, it also gave sir-crazy folks a reason to come out and party!
In its first year, In the Streets brought in 10,000 attendees. Now, more than four decades later, those numbers exceed 75,000! The event’s popularity remains constant, providing a way for all ages and interests to share in family-friendly fun and community camaraderie. It also keeps the foundational objective of allowing businesses and nonprofits throughout Frederick County to set up service booths and offerings of many kinds.
Next year’s In the Streets will take place on September 12, 2026, on Market Street, beginning at 9 a.m.
The Great Frederick Fair
There are many nice fairs to attend throughout Maryland, but you couldn’t assign a better adjective than “great” to describe this annual folly, which is why it’s part of the official title. Held every September, the Great Frederick Fair boasts a fantastically wonderful series of activities, events, and ovation-worthy options to charm any visitor of any age and interest.
The timeless testament to its impressive tenure, which goes back more than 160 years, is all the proof you need regarding the Great Frederick Fair’s telling greatness. Here you can enjoy an array of multifaceted experiences, from agricultural and 4-H pursuits to demos, competitions, and more. Foodies won’t be disappointed by the fine selections of profuse provisions to savor, and kids of all ages (including those of the 18+ distinction) will have a blast with authentic carnival rides, games, and other good old American classics. And don’t forget about the live entertainment and other special ticketed happenings throughout the fair’s multi-week run.
Next year’s Great Frederick Fair runs from September 18 through 26, 2026 on location of the Frederick Fairgrounds at 797 East Patrick Street, Frederick, MD 21701. Discover more details and all updated information for this year’s upcoming fair posted on their website at www.thegreatfrederickfair.com.
Catoctin Colorfest
While witnessing autumn’s natural artistry come to life is a treat in and of itself, there’s something especially alluring about the ambiance throughout Thurmont’s beautiful, bucolic canvas of changing colors. That’s one of the reasons why Catoctin Colorfest has been held here every second full weekend in October since 1963.
While the origins of the event may have started humbly, Catoctin Colorfest has emerged to become one of the largest outdoor craft shows on the East Coast. Over 350 vendors, locally based and venturing from faraway regions, comprise a vast and versatile lineup of participants each year. And attending crowds can reach as many as 110,000 attendees!
The profuse offerings here range from art, jewelry, home goods, knick-knacks, novelty essentials, and just about everything else you can imagine (or never even imagined in your wildest dreams)! Food and onsite entertainment also mark the lively scene in what can arguably be considered one of the county’s grandest pre-holiday seasonal events of the year.
Next year’s Catoctin Colorfest will take place on October 10 and 11. Attending is free, although a parking fee does apply. Shuttles will take you to the exact location of all active happenings. For more information about Catoctin Colorfest, including directions and vendor information, visit the website at www.colorfest.org.
National Clustered Spires High Wheel Race
Did you know that Frederick County, Maryland, is the only place where you can experience America’s only high-wheel bicycle race? Presented every July in historic Downtown Frederick, it’s the one and only National Clustered Spires High Wheel Race. For this event, riders hailing from all over the country come out to participate in the quarter-mile race, which begins at North Market Street (in front of Brewer’s Alley). The major draw, however, is admittedly the racers’ various modes of ride—they are none other than authentic (or masterfully replicated) 19th-century penny farthings, distinguishable by their large front wheels and smaller rear ones. While the race is a fun and thrilling delight for participants, it is just as much of a treat for the onlooking spectators crowding around to view the event live.
The next bi-annual race is slated for July 10, 2027. To learn more about the event and for the schedule when it becomes available, visit the website at www.highwheelrace.com.
Frederick County has so many boasting rights to its credit that it would be nearly impossible to list them all. That means any time is the perfect time to head on over and check out the vibrant and lively scene!
By LC Hermoza