Maryland may be one of the smaller states in the country, but when it comes to festivals, it packs an incredible amount of fun into every season.
Throughout the year, you can cheer on unusual competitions, step into living history, listen to world-class music, and enjoy some of the state’s most famous foods.
One weekend might have you watching colorful parades, while the next could be filled with costumed performers or creative displays unlike anything you’ve seen before.
Whether you’re planning a road trip, looking for a unique day out, or searching for your next great adventure, these unforgettable Maryland festivals deliver.
1. Maryland Renaissance Festival (Annapolis)
Time of year: Late August to Late October
Located in Annapolis, the Maryland Renaissance Festival transforms 27 wooded acres into the fictional 16th-century village of Revel Grove.
You can watch jousting tournaments, enjoy tavern performances and variety shows, see archery demonstrations, and browse more than 130 artisan shops.
What makes the experience especially memorable is the festival’s costumed cast of kings, queens, and other characters, along with giant turkey legs, mead, and lively music.
With dozens of daily shows, period-inspired architecture, and thousands of visitors on peak days, it ranks among the largest and most popular Renaissance festivals in the U.S.
2. National Hard Crab Derby (Crisfield)
Time of year: September
The National Hard Crab Derby celebrates Maryland’s seafood heritage in Crisfield, known as the Crab Capital of the World.
The main attraction is the famous crab races, where hard crabs race across a track as crowds cheer for their favorites.
You can also catch crab picking contests, a boat docking competition, live music, parades, fireworks, and beauty pageants that have been part of the festival for decades.
Launched in 1947 to promote the region’s seafood industry, the derby now draws thousands of visitors each year and shines a spotlight on the area’s maritime traditions.
3. Chestertown Tea Party Festival (Chestertown)
Time of year: Late May
Next comes the Chestertown Tea Party Festival, a lively annual event that celebrates colonial history with reenactments, parades, and Revolutionary War spirit.
Held along the Chester River, the festival commemorates the 1774 Chestertown Tea Party, when residents reportedly protested British policies by dumping tea into the river.
Today, you can watch a dramatic tea-tossing reenactment, browse colonial crafts, enjoy the parade’s marching bands, attend block parties, and join walking tours.
It’s a weekend full of tall ships, family activities, and live street performances, making it easy to spend an entire day exploring.
4. Maryland Sheep & Wool Festival (West Friendship)
Time of year: May
Held at the Howard County Fairgrounds in West Friendship, the Maryland Sheep & Wool Festival is one of the largest fiber arts events in the country.
It brings together more than 250 vendors selling yarn, fleece, spinning wheels, weaving supplies, and fiber art materials, making it a huge draw for knitters and crafters.
There’s more to see, including sheep shearing demonstrations, livestock competitions, wool fashion shows, spinning contests, and the popular parade of sheep breeds.
All of this has helped make the festival a major attraction since 1973, drawing thousands of attendees each year and showcasing every stage of the wool-making process.
5. Autumn Glory Festival (Oakland)
Time of year: October
If you’re looking for fall scenery and small-town charm, the Autumn Glory Festival in Oakland delivers.
The festival is famous for showcasing Garrett County’s brilliant autumn foliage, with scenic driving tours winding through forests where tall trees light up the landscape.
You can also watch the Grand Feature Parade and Annual Fireman’s Parade, explore corn mazes, discover gems at the Antique, Vintage & Maker Market, and visit art exhibits.
With its spectacular leaf-peeping opportunities, it’s no surprise that the festival is one of Maryland’s most celebrated fall traditions.
6. PEEPshow (Westminster)
Time of year: Late March
Each spring, the PEEPshow in Westminster celebrates creativity with hundreds of artistic displays made from the classic marshmallow PEEPS candy.
The exhibition showcases detailed dioramas, sculptures, and mosaics inspired by famous movies, historical events, Maryland landmarks, and pop culture characters.
While exploring, you can buy votes for your favorite creations and see entries made by local students, families, artists, and community groups.
If you enjoy unusual traditions, humor, and an impressive amount of marshmallow candy, this event is well worth a visit.
7. Maryland Seafood Festival (Sandy Point State Park)
Time of year: Mid-September
For fresh seafood and waterfront views, head to the Maryland Seafood Festival at Sandy Point State Park.
It’s best known for serving Maryland favorites like steamed crabs, crab soup, crab cakes, oysters, and other local seafood while offering sweeping views of the bay and bridge.
There are also popular themed contests like oyster shucking, competitive eating, and crab picking, giving you plenty of opportunities to cheer on competitors.
Altogether, it’s a celebration of the flavors, traditions, and waterfront lifestyle that make the Chesapeake Bay region unique.
8. Ridgely Strawberry Festival (Ridgely)
Time of year: May
Another local favorite is the Ridgely Strawberry Festival, held annually at Martin Sutton Park.
It celebrates the region’s agricultural heritage with fresh strawberry shortcake, strawberry smoothies, and plenty of locally grown berries.
Along with the treats, you can check out craft and vendor booths, watch the parade and Strawberry Chase 5K Run, enjoy live music, and take part in family-friendly activities.
At its heart, it’s a sweet celebration of small-town life, local traditions, and one of the state’s most famous spring harvests.
9. DelFest (Cumberland)
Time of year: May
Rounding out the list is DelFest, a music festival held at the Allegany County Fairgrounds in Cumberland.
Founded in 2008, the festival is known for bringing together top bluegrass, roots, Americana, and jam-band performers from across the U.S.
You can spend the day enjoying concerts, music workshops, yoga classes, and the Vending Faire, where vendors sell everything from clothing to musical instruments.
With past performers including The Del McCoury Band, Béla Fleck, and Sam Bush, DelFest has become one of the country’s most respected roots music festivals.
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