Maryland Festivals and Events

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After 15 years of exploring, the author creates his list of the best Maryland festivals and events. Read on for suggestions on what you must do when traveling through the Mid-Atlantic states.

Maryland has a deep history spanning hundreds of years. Native Americans lived here in large numbers after the last ice age. European settlers started laying down roots in the 1630s, and in 1788, Maryland was granted statehood. Some festivals and events spotlight Maryland’s history, and some are making history of their own.

Historic Fells Point in downtown Baltimore on a sunny day. Photo by Kurt Jacobson

During my first year in Maryland, my wife and I spent many weekends exploring restaurants, small towns, festivals, and events. Within a couple of years, we found several of the best things to do, see, and eat. This list is compiled from 15 years of traveling throughout Maryland.

A Famous Bluegrass Music Festival

One of the first outdoor music festivals we encountered was DelFest, named after Del McCoury, a famous bluegrass musician. We attended part of the three-day festival held in Cumberland, MD, at the Allegany County Fairgrounds. It was a good day to attend as the previous day had been fairly wet. The remaining mud puddles inspired young and old to play in the mud, making for an amusing day while the bands played on.

DelFest is a must for Bluegrass music lovers. Photo by J Strausser

The music, food, and beverage lineup was good, and everyone had a great time. Some regulars choose to camp in the area next to the fairgrounds. Restrooms and showers are provided for both tent campers and RV campers. A kid-friendly family camping area is perfect for a calmer experience. For an upscale camping option, epic glamping is a fun way to stay. We chose a more common lodging choice, staying at a hotel nearby, and were happy with that decision. DelFest takes place over four days each May.

Art, Music, and Hons

Baltimore has a thriving arts scene, and one of the premier events is Artscape. This free 3-day event is held each August in the Bolton Hill/Mt. Vernon neighborhoods. Many types of art are on display and for sale by artists from near and far. The festival offers live music most days and nights at various stages.

Artscape on a typical hot sunny day. Photo by Kurt Jacobson

Dozens of food and beverage vendors take care of hungry and thirsty art fans. We love the vibrant community spirit that includes folks from all walks of life. It’s usually quite hot and humid, so consider coming after 5 pm when it’s generally cooler, and plan on enjoying a good meal, shopping, and entertainment.

We learned about Baltimore’s Hon culture, where women show off big hair, sunglasses, colorful dresses, and plenty of makeup. Although the Hon Fest officially ended after the 2023 event, Stacey Hurly from the Baltimore Hon Hive is committed to reviving it. Though in the early stages of planning, keep an eye out for the return of the Hons on the Baltimore Hon Hive’s Facebook page.

HonFest is where the participants have as much fun as the crowd. Photo by Kurt Jacobson

Over on the Eastern Shore

One of the best festivals my wife and I have found is the Waterfowl Festival in Easton. This three-day event each November celebrates Maryland’s Eastern Shore duck and goose hunting heritage. This festival is not just for duck and goose hunters. With a wide variety of family-friendly events like dock jumping dogs, cornhole tournaments, fly fishing demos, art market, live music, raptor demos, and much more; this free event is a crowd pleaser.

I thought this little owl was among the most interesting raptors at the Waterfowl Festival 2022. Photo by Kurt Jacobson

Chestertown is one of the Eastern Shore’s most historic towns. In 1782, George Washington helped start Easton’s college, which is named after him. Each November, the Sultana Downrigging Weekend Tall Ship and Wooden Boat Festival celebrates nautical history when many a tall ship sailed into Chestertown’s colonial-era port. The weekend is packed with tall ship rides, a tall ship open house, wooden boats on display, fireworks, a tall ship parade, and plenty of food and drink.

I loved being able to tour historic tall sailing ships at the Downrigging Festival. Photo by Kurt Jacobson

Parking is a bit tricky, but I had luck parking on the north side of downtown near Casa Carmen Wines. To get the most out of your visit, try walking the downtown core and exploring the shops and restaurants during the festival. Stop at the Kent County Visitors Center at 122 N Cross St for festival information, clean restrooms, a historic walking tour map, and parking tips.

Festivals and Events in Baltimore

Horse racing fans will have undoubtedly heard of the Preakness Stakes held at Pimlico Race Course each May. What might be as popular these days as the horse races is the InfieldFest, now known as the Preakness Live. The Maryland Jockey Club started this music and drinking event to attract new and younger guests in the 1970s. During the early years, attendees could bring their own alcohol into Pimlico. Things got out of hand, and Pimlico banned outside alcohol in 2009. Beer drinking is still allowed and going strong as fans in the infield tend to be more interested in the music and beer than in horse racing.

High-speed fun at the Preakness Stakes Race. Photo courtesy of the Stronach Group

It’s good to know that horse racing still is the main draw at Pimlico. There’s a colorful history of horse racing in Baltimore. The first Preakness race was held on May 27, 1873, in honor of the horse of the same name who had won the Dinner Party Stakes in 1870. Since then, many riders have basked in the glory of winning, including seven African Americans, the first, Willie Simms, in 1898, with several others taking second place or lower finishes in subsequent years. The Preakness isn’t for everyone due to the prices, parking, and crowds. I’ve only attended the My Lady’s Manor Steeple Chase races in Jarretsville and love the smaller crowd and up-close experience.

Coming into the jump at full speed. Photo by Kurt Jacobson

Secretariat was possibly the most memorable racehorse of the last 55 years. This amazing horse won the coveted Triple Crown in 1973; only four horses have won it since then.

Holiday Special Events

Before visiting Salzburg, Austria, I visited a Christmas Village market in Denver. When we found out the Inner Harbor in Baltimore has a similar Bavarian-style Christmas market, we had to go. Each year’s Christmas Village in Baltimore is different, but there are usually 20 to 30 vendors.

Grab a glass of hot glüwein and explore the vendors to find presents or keepsakes. I’ve seen handmade toys at the market that take me back to my grandparent’s home, where antiques were the bulk of their possessions. Christmas ornaments are sold at one or more vendor’s stalls each year. The event runs from around Thanksgiving to December 24.

What’s not to love about a Christmas Village Market? Photo by Kurt Jacobson

Garden Glow is a crazy popular Halloween event. Ladew Topiary Gardens in Jarrettsville is usually known for the gardens, hiking trails, historic home tour, and butterfly pavilion. But in October, the gardens host some of the coolest carved pumpkins I have ever seen. All sorts of spooky carved pumpkins are on display, and you can even watch master carvers at work.

Uncommonly cool carved pumpkins. Photo by Kurt Jacobson

My favorite pumpkin from 2023 was a rendering of Edgar Allen Poe. The sheer number of carved pumpkins glowing at night was a sight to behold. It took us about an hour to see all the pumpkins, light displays, and other attractions. Decent food trucks and the onsite café cater to hungry participants, and a wine tent was an excellent addition to the food and beverage vendors. If you want to attend, buy your tickets as early as possible since the event sells out weeks ahead of time each year. Tickets usually go on sale around the first of September.

We had a great time at Ladew’s Garden Glow in 2023. Photo by Kurt Jacobson

Not Been There Done That…Yet

Frederick is one of my favorite towns in all of Maryland. They used to have a wine festival, but COVID seems to have killed it. When I asked the local visitors’ center about similar festivals, they told me about the Maryland Craft Beer Festival. In 2023, over 60 craft breweries showed up for the event held at Carroll Creek Linear Park. The park is along Carroll Creek in the center of Frederick and is an excellent place for such an event. Maybe I’ll get to go in 2024? The festival is held in mid-May each year.

Maybe someday, the wine festival will return to Frederick, MD. Photo by Kurt Jacobson

Westminster has the Carroll County Farm Museum, which hosts several fun events. I’ve been to farm heritage events and even a blues festival there. I didn’t realize they have the Maryland Wine Festival on the museum grounds, which has been held one day in September for the past 39 years. Maryland has over 80 wineries; some make excellent dry wines, while others focus on fruity wines. Boordy Vineyards is one of the oldest wine producers in the Mid-Atlantic and will be at the 2024 Maryland Wine Celebration. Boordy ranks as a favorite amongst locals.

A cute wine-tasting table at Boordy Vineyards. Who is that photographer in the window? Photo by Kurt Jacobson

Guests at the festival can taste wines on-site or purchase wine to take home. I plan on attending this September to see if it’s as good as the previous press indicates.

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Visiting Maryland Festivals and Events

This list is just a tiny sampling of Maryland’s festivals and events to get you started. I hope you have a blast and come back for more. We invite you to explore Wander With Wonder for more things to do while visiting Maryland or other parts of the Mid-Atlantic region.