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You’ll Totally “Fall” for These Exciting Autumn Events in Maryland

You’ll Totally “Fall” for These Exciting Autumn Events in Maryland

National Folk Festival in Salisbury

Summer in Maryland is absolutely a thrill. Beautiful beaches, exciting cities, and mountain views entice us all to go explore our state. But fall is really when Maryland’s vibrancy awakens. We’ve found fall events in Maryland that showcase our state’s rich culture and highlights each region’s artists and community. So gather up your friends and family, hit the road, and kick the season off with some fun!

Sunfest — Ocean City, MD

September 30 – October 3

This annual OC tradition is like nothing else! Sunfest spans four days with live music, artists on the Inlet, and of course Ocean City’s amazing food. This event is known to Eastern Shore  locals as the event of the year and the close of the summer season.

Sunfest
Photo Credit: Ocean City Tourism

If you want to get away from the crowd for a while, drive down Stephen Decatur Highway for a few miles to get to Assateague National Seashore. Stop at Hooper’s Crab House on your way out of Ocean City for a great end-of-summer crab experience. 

Maryland Wine Festival — Westminster, MD

September 18-19

Located on the grounds of the Carroll County Farm Museum (worth a visit in and of itself), this decades-old event is a showcase of Maryland wine. With food and artisan vendors, along with live music all weekend, the Maryland Wine Festival promises a great time to relax, have a picnic and enjoy!

Maryland Wines
Photo Credit: The Maryland Wineries Association

This is an enormous event that draws people from all over the state. And while it’s obviously labelled as an adult-oriented event, young children are permitted to attend. Stop by Hoffman’s Ice Cream on the way home for a delicious treat!

In the Streets in Frederick — Frederick, MD

September 11

Spanning over seven city blocks, In The Streets has been a Frederick tradition for nearly 40 years. This festival highlights all the businesses, restaurants, craft beverages, vendors ,and entertainment that Frederick County has to offer.

In the Streets in Frederick Maryland
Photo Credit: Celebrate Frederick

Traffic is shut down for the day, which makes for easy walking and browsing the unique restaurants and shops along historic Market Street and cross streets. While you’re in the area, take in more autumnal beauty with a hike in Catoctin National Park, Cunningham Falls, or Gambrill State Park.

The Maryland Renaissance Festival — Crofton, MD

Every Saturday and Sunday from August through late October, starting August 28th and ending October 24th. 

If you’ve never attended what’s locally known as “Renn Fest,” then you are missing an incredible experience! Be transported back in time to a Tudor village and enjoy all it has to offer you.

Renn Fest Actors
Photo Credit: Shutterstock

From food and artists, to celtic-inspired musicians and Shakespearean shows, Revel Grove is a bustling and exciting place to spend the day. The youngest lords and ladies will love the jousting and kid friendly shows and games, while their parents may turn into a court jester at one of the many village pubs!

Looking for more opportunities to step back in time? Cross the South River bridge at Route 2 to get to Historic London Town and Gardens, a “lost” colonial seaport in Edgewater, MD.

Colorfest — Thurmont, MD

October 9-10

Colorfest is a well known event in Frederick County, and for good reason. It takes over most of the streets in Thurmont! This event centers around Thurmont Park, but spills out onto Catoctin Furnace Road. Colorfest hosts artists and crafters, but also live music, food, and games all through the small town. As Thurmont is known as “The Gateway to the Mountains,” you will be surrounded, truly, by color!

Once you’ve been able to soak it all in, head to Catoctin Orchard for freshly made pies and delicious produce.

Hard Crab Derby — Crisfield, MD

September 3-6

The Hard Crab Derby is the jewel of the Eastern Shore, and the whole weekend draws thousands of visitors to Somers Cove Marina. With amusement rides, concerts, a 10k crab walk, crab parade, crab picking, and cooking contests, it truly is an all-around Maryland watermen festival!

Two people eating crabs
Photo Credit: Shutterstock

The end of the festival is the crab derby, where watermen literally race their crabs on a track. Before you leave the heart of the Chesapeake, take a ferry ride to Smith Island and pick up an authentic Smith Island cake to bring home with you (or devour in the car).

National Folk Festival — Salisbury, MD

September 10-12

Held in the center of Salisbury along the streets of the Wicomico River, the National Folk Festival encompasses all the things folk should be—a celebration of heritage. This includes artisans and musicians of many ethnicities and backgrounds sharing their culture.

National Folk Festival in Salisbury
Photo Credit: National Folk Festival in Salisbury

Some of the crafters and demonstrations will be traditional blacksmiths, quilters, and weavers from native Maryland tribes. The event is a family-oriented exposure to many different cultures through their art and their food.

National Folk Festival in Salisbury
Photo Credit: National Folk Festival in Salisbury

While in Salisbury, take in the Ward Museum of Wildfowl Art to see more folk art displays or visit the Salisbury Zoo!

Autumn Glory Festival — Oakland, MD

October 13-17

Few places are more stunning in the fall than Deep Creek Lake, and so the Autumn Glory Festival is perfect for every autumnal lover. Oakland is well-known for its gorgeous fall foliage — its natural beauty has been recognized by Good Housekeeping, Travel & Leisure, Readers Digest, and more!

Autumn Glory Festival
Photo Credit: Autumn Glory Festival

Downtown Oakland is taken over by craft vendors from Wednesday through Sunday, as well as Maryland-made gifts and country-style wares. There are daily foliage tours and corn mazes, and even a float contest on Saturday.

Boat on a lake with beautiful orange leaved trees surrounding the lake
Photo Credit: Doris Rafaeli

A visit to Deep Creek is definitely warranted if you come to Autumn Glory, but a stop at Swallow Falls’ beautiful state park is also worth a visit!


Lead Photo: National Folk Festival in Salisbury

About the Author

Meghan Cannon

Meghan Cannon is a Frederick County resident and teacher. Active Civil Servant, she is the Chair of Frederick’s In The Streets Committee. Meghan is a mom of two. You can find her Maryland writings about locations, tourism and oddities on her Instagram account, MarylandMyMaryland.

Maryland Road Trips is a part of Postern Publishing.
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