8 Offbeat Maryland Towns To Visit In 2025

Maryland may not be your first choice for a 2025 vacation—that is, until you hear about the weird and wonderful attractions in its small towns. Skip Baltimore to discover a huge oyster festival in a compact coastal community, an unfinished Biblical replica in the Maryland Panhandle, and a herd of feral horses on an idyllic island. Seeing those and other sights can fill the whole year, so do not worry about what month you visit offbeat Maryland; make sure you visit sometime in 2025.

Leonardtown

You could call Leonardtown the pearl of Maryland. That is not just because it is a small, stunning town on MD's coast but because it annually hosts MD's largest oyster festival. The U.S. National Oyster Festival has been feeding many thousands of mollusks to many thousands of Marylanders since 1967. It was conceived by nearby Lexington Park's Rotary Club and now takes place each October at the St. Mary's County Fairgrounds.

In addition to the shameless consumption of oysters, the fest features a shucking competition that draws competitors from across the country. 2024's winner shucked 24 oysters in just over 2 minutes. While shelling out for this festival, check out another hard Leonardtown attraction: Moll Dyer Rock. That is where the titular woman supposedly froze to death after being accused of witchcraft in the 17th century. Although 2025's edition has already passed, Moll Dyer & Local Legends Weekend runs each February to honor Dyer and wider Leonardtown folklore.

Frostburg

Frostburg is full of far-out festivals in far-out western Maryland. They include the Appalachian Festival, a celebration of Appalachian culture set to have its 20th edition from September 18 to 20, 2025, and Pirates Ahoy!, a pirate-themed kids' event held in July and sponsored by the Frostburg State University Children's Literature Center.

Curiously and cutely, many Frostburg fests are dog-based. The Frostburg Dog Splash brings pups to the Frostburg Pool in September, while the Western Maryland Craft Beverage Festival trades beer money for animal shelter space in late August or early September. Whichever offbeat event you attend, be sure to vacate for a few minutes to see God's Ark of Safety, an attempted Biblically-sized replica of Noah's Ark that began construction in 1976 and is still just a frame—but a giant one along Interstate 68.

Westminster

There is no dog show in Westminster, Maryland. But there is a PEEPshow—and note the emphasis on PEEP. Each year around Eastertime, this small city gets covered in marshmallow PEEPS for the Annual PEEPshow. Thousands upon thousands of PEEPS are fashioned into elaborate sculptures and displayed in the TownMall of Westminster.

Past PEEPshowings include Winnie the Peep, The Very Hungry Caterpeeper, and PEEPachu. Spectators vote on the best ones. 2025's PEEPshow is set to run from April 11 to 21, but if you are unable to attend, take a peep at Westminster's other unique fests, like the Westminster Flower & Jazz Festival in May and Westminster Oyster Stroll in October.

Chestertown

In 1774, Chestertown had its own Tea Party, where townsfolk rebelled against British rule and, according to legend, cast British tea into the bay like Bostonians had done the year prior, helping to spur the American Revolution.

More than 250 years later, Chestertown honors that alleged tea-chuck with the Chestertown Tea Party Festival. It runs during Memorial Day Weekend and features food, drinks, colonial crafts, strolling musicians, street performances, fun runs, a parade, and, of course, a tea toss reenactment. You can pair that throwback fair with throwback fare at Modern Stone Age Kitchen, which is an ancestral cooking company run by an archaeologist.

Havre de Grace

You have likely heard of duck festivals, where thousands of rubber ducks are raced down a river for cheering and betting spectators, but how about a duck decoy festival? Uniquely named Havre de Grace hosts the uniquely-themed Decoy & Wildlife Arts Festival. For over four decades, it has celebrated hunting decoys, especially those that resemble ducks, which are carved during the festival's many competitions. 2025's fest is scheduled to run from May 3 to 4 at the STAR Centre.

While there, make sure to visit the Havre de Grace Decoy Museum, which "houses one of the finest collections of working and decorative Chesapeake Bay decoys ever assembled." Havre de Grace is unsurprisingly called the "Decoy Capital of the World."

Berlin

Home to just over 5,000 people on Maryland's Eastern Shore, Berlin has about 200 residents for every offbeat festival. Chief among them are the Berlin Bathtub Races, where wheeled bathtubs race down Main Street each June; the Berlin Peach Festival and Berlin Chili Pepper Festival, a one-two punch of sweet and spicy landing in August; and ICE ICE Berlin & Tree Lighting, a pre-Christmas ice sculpture carving and tree lighting celebration. One quirky attraction that you can see year-round is a herd of feral horses, which lives outside town on Assateague Island.

Annapolis Junction

Annapolis Junction is an unincorporated community known, if known at all, for the National Cryptologic Museum. Ironically, it is a collection of history's most classified coding and code-breaking equipment and techniques that is open to the public. Visitors can see, among many other artifacts, a series of Enigma machines of the kind Alan Turing cracked during WWII and was depicted in the Oscar-winning film The Imitation Game. The National Cryptologic Museum adjoins NSA Headquarters at Fort Meade, which, unlike Annapolis Junction, is a census-designated place with over 9,000 cataloged people.

Princess Anne

Maryland has a tradition of unusual New Year's Eve "drops." Instead of a giant ball, Hagerstown drops a donut, the aforementioned Havre de Grace drops a duck, and Princess Anne drops a muskrat. Named Marshall, this taxidermized rodent is dressed in a green top hat and cape and lowered at midnight from a 30-foot-tall contraption designed by a NASA engineer. Aside from the climactic Muskrat Dive, Princess Anne's New Year's Eve celebration features or has featured live music, street dancing, games, tarot readings, face painting, oyster shucking, and a cider toast. See what is on tap this year.

Maryland’s Most Eccentric Towns Await in 2025

Though Baltimore certainly has its quirks, Maryland's most offbeat locales are small towns. This is evident by their multitude of odd attractions, some that run annually and others that run year-round. Included in the former category are Leonardtown's Oyster Festival, Chestertown's Tea Party Festival, and Princess Anne's Muskrat Dive. Included in the latter are Frostburg's Ark and Havre de Grace's Decoy Museum. Which will you visit first during your 2025 offbeat Maryland vacation?