Maryland
8 Most Eccentric Towns in Maryland
Although Maryland is the ninth smallest state by size, it is surprisingly diverse in festivals, history, and natural landmarks, particularly in its small towns. Antique auctions, bathtub races, banjo competitions, waterfall hikes, and alpaca farms are just a few of the exciting experiences that await. If you want to mix up your routine and visit a town with one-of-a-kind attractions, keep reading to discover your next adventure.
Berlin
Named by the Smithsonian as one of the “20 Best Small Towns to Visit”, bathtub races, honkey tonks, and colonial mansions are just a few of the attractions that set Berlin apart. One of the town’s strangest traditions takes part on July 7th, a bathtub race where competitors dash through the streets in tubs and barrels, vying for the title of fastest tub racer. The Globe is another unbeatable attraction, serving as a restaurant and bar while doubling as a live music venue, comedy club, or movie theater, depending on the night.
The Rackliffe House is a fascinating historic landmark, a brick mansion over 300 years old that has witnessed the passing of Barbary Pirate Ships, Spanish Galleons, and the Revolutionary War, serving as a museum today. Keep your eye out for funky shops and restaurants downtown, including Fins Ale House and Raw Bar, Blacksmith Restaurant, and Jeffery Auxer Designs Glass Studio.
Oakland
There is always something going on in Oakland, with the town hosting countless annual events throughout the year. The Maryland State Banjo, Mandolin & Fiddle Championships, Oakland Winter Fest, Little Yough Summer Music Festival, and Autumn Glory Grand Feature Parade are just a few to check out.
Ever dreamed of meeting an alpaca? You can do so at Alpaca Acres Farm and Fun by scheduling a meet and greet, as well as enjoy the farm’s family-friendly activities and gift store. To see the tallest free-falling waterfall in the state, spend a day hiking at Swallow Falls State Park, home to 53-foot tall Muddy Creek Falls.
Chestertown
Those who love eclectic finds and antiques must spend a few days at Chestertown, home to the renowned Dixon’s Crumpton Auction. Crumpton’s, a third-generation auction company, hosts fast-paced antique auctions. It is not uncommon to sell 200 antique items per hour, allowing visitors to nab a vintage treasure.
Chestertown’s arts & entertainment district is another great place to walk away with a one-of-a-kind souvenir, full of art studios, galleries, and art centers. Barn Artist Studio, Hegland Glass Gallery, and Garfield Center for the Arts are just a few artsy spots worth checking out. Those wanting to get some exercise can start their morning off running, walking, or biking on the 2-mile Wayne Gilchrest Rail Trail.
Leonardtown
Leonardtown can be divided into several diverse districts, the Leonardtown Wharf, Fenwick Street, Leonardtown Square, and the Arts & Entertainment District, being just a few. At the Wharf, visitors can admire waterfront views and rent a kayak or canoe to explore the waters.
Fenwick Street is home to eclectic shops and boutiques, Board & Brush, North End Gallery, and David’s Flowers being just a few to check out. Check out the War Memorials Garden in Leonardtown Square, one of the few provincial town squares remaining, while the Arts & Entertainment District is perfect for attending a class, workshop, or occasional town market.
St. Michaels
Located on a narrow strip of land along the Miles River, near the Chesapeake Bay, St. Michaels is a lively coastal town. Visitors can explore the harbor by renting a paddleboard or kayak, going on a sailing charter, or enjoying an afternoon cruise. To learn more about the Chesapeake Bay, travelers can spend a morning at the Chesapeake Bay Maritime Museum, situated on an 18-acre waterfront campus.
For a meal with a view, there are several waterfront restaurants to choose from, including Stars and Blu Miles. All December long, visitors can enjoy St. Michael’s holiday events, including a Christmas and Lighted Boat Parade, Breakfast with Santa, and New Years Eve celebrations, so keep your eye on their calendar!
Sykesville
Sykesville boasts one of the state’s most fascinating downtown districts, recognized as both a National Trust for Historic Preservation District and a National Main Street District. A few of the historic landmarks to check out include the Old Main Line Visitors Center and Post Office, the Sykesville Town House, and the Sykesville Gate House Museum.
The Little Sykes Railway Park is another fun attraction, a miniature train from 1949 that runs through Sykesville’s 2-acre park. Those wanting to head outdoors can make their way to the Patapsco River, popular for both tubing and fishing.
Thurmont
Locals in Thurmont often refer to it as being Maryland’s “Gateway to the Mountains”, conveniently situated near the Catoctin Mountains. Those wanting to explore these nearby mountains must visit Catoctin Mountain Park, home to 25 miles of hiking trails, historic exhibits such as the Sawmill and Blue Blazes Whiskey Still, and places to camp, picnic, rock climb, and fish.
The historic village of Catoctin Furnace is another one of Thurmont’s attractions, featuring 65 houses, a church, a school, and a store to explore. To see a 78-foot cascading waterfall, Cunningham Falls State Park is another outdoor recreational option, also home to a 43-acre man-made lake.
Chesapeake City
Located along one of the world’s busiest canals, Chesapeake City is a lively waterfront town with many bars, 19th-century historic buildings, and a brewery to discover. Explore the canal up close along the Ben Cardin C&D Canal Trail, a 17-mile trail that winds along the entirety of the canal.
Bayheads Brewing Company, founded in 2016, is a local brewery with a rustic-style taproom where visitors can enjoy craft beer, cider, whiskey, or wine. For luxury chocolates and candies, check out Chesapeake Candy Works. Want to get on the water? Consider a tour with Chesapeake Water Tours, who will take you on an exciting cruise through the bay.
Final Thoughts
Concluding our tour of these eight eccentric towns, it is clear that Maryland has a unique side that sets it apart. No matter where your interest lies, whether it be in hiking, maritime history, or souvenir shopping, each of these towns will give you an unforgettable vacation or weekend away. So, dust off your suitcase and prepare to explore the quirky, unforgettable side of Maryland!
Maryland
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Maryland
Philadelphia car rally driver accused of hitting 2 separate troopers in Maryland
PRINCE GEORGE’S COUNTY, Md. (7News) — A Philadelphia man is facing charges after authorities said he hit two Maryland State troopers during illegal car rally events in Prince George’s County.
Isaiah Vega, 19, faces first-and second-degree assault and assault on a law enforcement officer, according to Maryland State Police (MSP). He is being held without bond.
Troopers struck during attempts to stop vehicle
The incidents date back to Nov. 16, 2025, when investigators with the Maryland Car Rally Task Force spotted a black Chrysler 300 without registration plates near MD 704 and Glenarden Parkway in Glenarden.
MSP officials said Vega fled during an attempted traffic stop and struck a trooper who was outside of his vehicle. That trooper was not hurt.
A short time later, officers found the same Chrysler at a gas station on Crain Highway in Bowie. During another attempt to stop the car, investigators say Vega hit another trooper before fleeing again.
The second trooper was taken to a hospital and later released.
SEE ALSO | Attending an illegal car rally could soon mean jail time in Prince George’s County
Alleged driver identified, arrested months later
Through an investigation involving multiple agencies, including the U.S. Marshals Service, Virginia State Police, and Pennsylvania State Police, authorities identified Vega as the driver.
He was arrested on March 23 in Prince George’s County.
Maryland
‘Riots,’ violence, questions over privately run youth facility in Maryland
KEYMAR, Md. (WBFF) — A privately operated youth treatment and foster home facility in rural Carroll County is facing renewed scrutiny after repeated emergency calls, violent incidents, and growing concerns from local law enforcement over whether the state’s current model is failing some of Maryland’s most vulnerable children.
Silver Oak Academy, a staff-secured residential treatment campus that does not use fencing, locks, or restraints in Keymar, has generated more than 100 calls for service since January 2025, according to public records obtained by Spotlight on Maryland.
Police records obtained show 35 incident reports resulted from those calls, including arson, destruction of property, assaults, escapes of at-risk juveniles and motor vehicle thefts.
Silver Oak Academy in Carroll County, Md., a privately operated foster setting for juveniles under state care. (Steve Pierce/Spotlight on Maryland)
Carroll County Sheriff Jim DeWees told Spotlight on Maryland that his office has been swamped with emergency calls for service from Silver Oak Academy staff and juveniles since it was reopened in late 2024 after a cycle of failed relaunches and abrupt closures.
Dana Rexrode, executive director for Rite of Passage’s eastern district, which includes Silver Oak, disputed characterizations made by DeWees that the alternative environment was spiraling out of control. She said the “open campus” model focused on therapeutic intervention rather than confinement.
“We don’t have locks on our doors,” Rexrode told Spotlight on Maryland by Zoom on Thursday. “They [foster juveniles] move freely with direct supervision around the campus. We don’t use any sort of mechanical restraints.”
The Maryland Department of Human Services and the Department of Juvenile Services oversee Rite of Passage’s contract and enforcement of Silver Oak. DJS did not accept Spotlight’s interview request, while DHS said Silver Oak is on its ‘hot list’ of facilities.
‘Overtaking the campus’
A February 2025 emergency call Spotlight on Maryland obtained included a female staffer who told the dispatcher that teens were “overtaking the campus.”
“They have rocks,” said the caller in February 2025. “They’re breaking windows.”
“I’ve had a youth spray a fire extinguisher in a staff’s face, and we are not able to manage it,” the caller said in a panicked tone.
Three Silver Oak juveniles, ages 13, 14, and 17, were arrested in that incident.
DeWees said the incident was, at the time, the second major fight in just two weeks. The sheriff added that at least eight assaults have been linked to the facility since January 2025.
The latest flashpoint came last week.
Body-worn camera footage obtained by Spotlight on Maryland on Thursday – matched with dispatch audio reviewed – revealed a staff member calling 911 again to report that three juveniles at the facility were actively setting fires on campus.
Go, go, run, run,” said the Silver Oak staffer. “We have three youths setting things on fire at our campus.”
When asked by dispatch whether anyone was in danger, the staffer promptly responded: “Honestly? Yes.”
Carroll County Sheriff’s Office offense/incident report for a Silver Oak Academy call on March 24, 2026 (Carroll County Sheriff’s Office)
Click here to view the PDF file
A staffer told Carroll County deputies that Silver Oak teens “threw a flaming book” at him as he attempted to get the juveniles under control.
‘Escalated and elevated’
Rexrode described the most recent incident that Carroll County Sheriff’s Office incident reports dispositioned as a riot, malicious burning, arson, and second-degree assault, as “three students who became escalated and elevated.” She said that staff were able to de-escalate the situation and safely return the teens to their dorms within about 45 minutes.
“I’m not sure three students constitute a riot,” Rexrode said.
ALSO READ | Maryland DJS workers beg leadership for help in leaked emails: ‘Continue to be in danger’
DeWees said he sharply disagrees with that assessment.
We’ve had riots out there where we’ve had multiple units respond to take over the facility and had multiple arrests,” DeWess said. “Our understanding is that it had been going on for quite some time. It was about 50 to 55 minutes later that they finally decided it was so much out of control that they had to pick up the phone and dial 911.”
Despite making arrests during the incident two weeks ago, the Maryland Department of Juvenile Services released the teens back to Silver Oak’s custody within days.
Carroll County Sheriff Jim DeWees told Spotlight on Maryland on Tuesday, April 7, 2026, that his office has been overwhelmed with calls for service related to incidents that have occurred at Silver Oak Academy. (Steve Pierce/Spotlight on Maryland)
State records showing Silver Oak has the capacity to house 96 male juveniles ages 14 to 18. The privately run facility is overseen as an interagency partnership with the Maryland Department of Human Services and the Department of Juvenile Services.
More recent local emergency management records describe the current program as serving up to 24 male youths with high-acuity mental health and trauma-related needs in a foster care-like environment.
Assault reported
DeWees said that despite more than 60 staff members, the population as the time of the recent incident was a low as six students.
“For the amount of staff that they have, I don’t think there have been more any more than 10 or 12 students there,” DeWees said.
ALSO READ | Schiraldi hired convicted murderer to help reform Maryland’s juvenile justice system
The sheriff asserted that staff have told him and his deputies that they are discouraged from contacting law enforcement while on duty and managing potentially violent situations internally.
We had a staffer walk into our office [on Monday] to report an assault,” DeWees said. “The staffer disclosed to us that they came here while they were off work because they were told not to come and make a call during the day because it’s not looking good for them if staff were claiming they were assaulted.”
Rexrode was asked by Spotlight on Maryland if staff and juveniles were safe, given the large number of calls for intervention from the sheriff’s office.
Dana Rexrode is the executive director of Rites of Passage’s eastern district, the private organization that operates Silver Oak Academy in Carroll County, Md. (Steve Pierce/Spotlight on Maryland)
“We greatly respect our staff and we encourage them to reach out to law enforcement if they feel that they need to do so,” Rexrode said.
Costs to taxpayers
Meanwhile, DeWees said that, besides being worried about the welfare of his deputies, he is alarmed by the costs of Silver Oak’s program to taxpayers.
According to public records reviewed by Spotlight on Maryland, Rite of Passage receives approximately $893 per day per youth housed at Silver Oak. Extrapolated out, that figure amounts to roughly $326,000 annually per occupied bed.
“I almost feel like the state is writing a blank check to Rite of Passage and they’re just simply cashing the checks,” DeWees said.
Rite of Passage is headquartered in Nevada. The organization operates similar alternative youth programs around the country.
ALSO READ | Maryland officials silent about housing juvenile offenders in hotels after alleged rape
Silver Oak operates on the site of the former Bowling Brook Preparatory School, a juvenile facility that long faced controversy, including past investigations into serious incidents and litigation involving a youth death and safety failures. Another private organization operated the location during the time of the incident.
DeWees said that prior youth death years ago remains top of mind.
“What keeps me up is I’ve seen that particular facility, under that particular group [Rite of Passage], not work,” DeWees said. “It’s absolutely a recipe for disaster.”
Do you have news tips about privately operated juvenile facilities that are funded by Maryland tax dollars? Send tips about this story or others to gmcollins@sbgtv.com or contact Spotlight on Maryland’s hotline at (410) 467-4670.
Follow Gary Collins on X and Instagram. Spotlight on Maryland is a collaboration between FOX45 News, WJLA in Washington, D.C., and The Baltimore Sun.
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