These 7 Maryland Towns Have The Most Unique Festivals

With its colorful past and vibrant present, it’s no wonder that Maryland has the best festivals. In a region once roamed by pirates, fought over in both the Revolutionary and Civil War, and later shaped by watermen, farmers, and immigrants, celebrations here mix history with plenty of fun. One weekend, you can step back in time to the court of King Henry VIII, the next you’re floating in a dinghy with pirates on the Chesapeake, and by fall you’re soaking in Catoctin Mountain color while browsing handmade arts and crafts. Here are seven of the most unique festivals in the Old Line State.

Maryland Sheep & Wool Festival, West Friendship

Everything you always wanted to know about sheep and wool, but were afraid to ask, the Maryland Sheep & Wool Festival has you covered. The largest and oldest festival of its kind in the United States, the annual event held annually on the first full weekend in May, draws over 50,000 visitors from across the U.S. and international vendors from the United Kingdom, Iceland, New Zealand, and South America.

Originally called the “Sheep and Wool Crafts Festival,” the inaugural event was held in the spring of 1974 as an agricultural fair with the sole purpose of promoting lamb and wool and educating sheep producers and the public about sheep and sheep products. In the ensuing years, while the festival’s mission has remained the same, the festival has blended serious livestock showcasing with a quirky fiber-artsy community spirit. From shearing demos and yarn crafts to entertainment, food, and rare livestock like 2025’s featured breed, the Valais Blacknose, known as the “cutest sheep in the world,” the festival is a spectacular celebration of all things sheep. The 53rd Annual Maryland Sheep & Wool Festival occurs May 2 and 3, 2026, at the Howard County Fairgrounds in West Friendship.

Antique and Classic Boat Festival, St. Michaels

The Antique & Classic Boat Festival and Coastal Arts Fair is a much-loved annual event in picturesque St. Michaels on historic Chesapeake Bay. The festival was launched in the late 1980s at the Chesapeake Bay Maritime Museum (CBMM). Boat enthusiasts, seasoned sailors, junior skippers, and even curious land-lubbers sail into town for the three-day event, one of the largest classic boat shows in the Mid-Atlantic region of the U.S. Traditionally held on Father’s Day Weekend, the 37th annual event took place from June 13 to 15, 2025, where visitors explored more than 100 cruisers, runabouts, and racers from various eras, as well as a variety of sport boats that were memorably featured in television and film in honor of this year’s theme “Boats in Movie and Television.” Other family-friendly activities at the event include a boat-building station, boating history talks, a scavenger hunt, boat rides, food vendors, and a beer truck.

National Hard Crab Derby, Crisfield

Celebrated in the town whose alter ego is the “Crab Capital of the World,” Crisfield welcomes the 78th National Hard Crab Derby on August 29 to 31, 2025. The festival kicked off in 1947, the brainchild of former “Crisfield Times” editor, Egbert L. Quinn, who wanted to celebrate, remember, and honor the rich crabbing history of Crisfield. Held annually on Labor Day Weekend, the National Hard Crab Derby features a crab cooking contest where food experts choose from four categories, like appetizers, soup/salads, main dishes, and crab cakes, a boat docking contest, crab races, a parade, and the time-honored tradition of crowning Miss Crustacean, Little Miss Crustacean, and Mr. Crustacean.

If the Labor Day crustacean celebration leaves you wanting more, head back to Crisfield on September 24, 2025, for the 48th Annual J. Millard Tawes Crab and Clam, an all-you-can-eat seafood extravaganza at Crisfield’s Somers Cove Marina.

Maryland Renaissance Festival, Crownsville

The Maryland Renaissance Festival is one of the largest and most beloved Renaissance fairs in the United States. The event is held in the small town of Crownsville, whose population of 1,300 residents swells to over 300,000 throughout the nine weekends during August, September, and October of “Ren Fest,” as it is known to devotees. Established in 1977, the jousting jamboree is held in a permanent 25-acre site that resembles a 16th-century English village called Revel Grove. The Maryland Renaissance Festival stands apart from other fairs in that it relies on the reign of Henry VIII and his six wives as the storyline for the event.

The setting and plot are just one part of the experience, as you’ll discover so much to see and do in the fictional village where more than 200 performers provide constant entertainment on stages and in the streets, as well as 140 merchants selling artisan crafts. There are over 42 food and beverage kiosks, five taverns, and a three-thousand-seat jousting arena.

The opening weekend of this year’s highly anticipated event is on August 23 to 24, 2025. No costume? No problem. There’s a costume rental booth on site where you can choose to be a wench or a fair maiden, a rogue, an outlaw, a knight, or a monk.

Chesapeake Music's Chamber Music Festival, Easton

This year, the Chesapeake Music Chamber Music Festival celebrated its 40th anniversary with a series of concerts by six world-class musicians on the theme of “Reflection and Celebration.” The event is sponsored by the non-profit organization, Chesapeake Music, every June, and performances are held in the Ebenezer Theater in the small town of Easton on Maryland’s Eastern Shore. The theater is a state-of-the-art performance space housed inside the former Ebenezer Methodist Church, built in 1856. In 2021, the Ebenezer Theater became the new home to Chesapeake Music. During the fall of 2025, the theater hosts numerous arts and cultural events, including three days of films as part of the Chesapeake Film Festival on October 10 to 12, 2025.

Pirates & Wenches Fantasy Weekend, Rock Hall

If dressing up like a pirate channels your inner buccaneer, Rock Hall, Maryland, is the place to drop anchor every August during the Pirates & Wenches Fantasy Weekend. The family-friendly weekend includes everything from a “most-wanted pirate” treasure home where festival goers search for seven pirates wandering around town, a sea shanty sing-a-long at the legion hall, a beach party with prizes for best-decorated dinghy, to a Buccaneers Ball at Waterman’s Crab House, a local restaurant and dock bar.

The town-wide theme party, which first set sail around 2014, has earned accolades as one of the stand-out events of the year. Attendees arrive by land or sea. The event offers ample space for dockage, anchoring, or raft-up options. This year’s fantasy weekend took place from August 8 to 10 on the waterfront in Rock Hall.

Catoctin Colorfest, Thurmont

What started as an autumn stroll through nature in Catoctin Mountain Park in the Blue Ridge Mountains in 1963 has grown into one of the largest outdoor arts and crafts festivals on the East Coast. Held annually on the second weekend in October, the colorful festival attracts about 125,000 festival goers to the small town of Thurmont, about fifteen miles south of Gettysburg, Pennsylvania. The two-day festival is the ultimate destination for art and craft lovers, showcasing local art, pottery, jewelry, crafts, live music, a German beer garden, and more. Colorfest occurs on October 11 and 12, 2025, from 9:00 AM to 5:00 PM. Admission is free.

From the state that gave you the fabulous “HonFest” in Baltimore, a lively street festival that celebrates the big city’s quirky “Hon” culture (think beehive hairdos, retro fashion, and cheeky charm), Maryland’s small towns are not to be outdone, each rolling out its own colorful festival. So whether you go for the food, the music, the costumes, or simply the friendly community vibes, be sure to check out a Maryland festival in a small town near you.