Main Events: Summer of '26!
June/July!
August!
The Running of the Bull in Dewey Beach, Del. is an absurd & ridiculous & comical affair. That’s why it’s so darn popular. Sat., June 27.
PS: There might be drinking involved here.
The Blessing of the Combines in Snow Hill, Md. Sat Aug. 1 begins with a specatular morning parade of oversized farm vehicles rumbling into downtown. A fun day-long block party after that. And yes, there really will be a blessing.
Get steamy! The big Tuckahoe Steam and Gas Show July 9-12 near Easton, Md. Living history performers and lots of old-time crafts on display along with a bevy of steam-powered classics.
The largest billfish tournament in the world Aug. 3-8 in Ocean City, Md. Landlubbers can get in on White Marlin Open action at daily parties with music, libations, and weigh-in views via big-screen TVs.
The USA Hot Air Balloon Festival at the Dover (Del.) Speedway grounds Fri/Sat July 10/11–tethered rides, balloon glow, DJ, vendors, kids zone, lots more.
The Chesapeake Bay Maritime Museum in St. Michaels, Md. throws a big Watermen’s Appreciation Day party with food, music, boat docking, more–Sun Aug 9.
The Snow Hill (Md.) River Fest at Sturgis Park Sat July 18 will have anchor tosses and homemade river raft races and live music and beer and orange crushes and food and corn hole and lots more.
The Pirates & Wenches Fantasy Weekend in Rock Hall, Md. Aug. 7-9 will have lots of full of music and family fun, but with a smidge of mayhem in the mix. Sea shanty sing alongs, rum tastings, beach parties, a “Buccaneer’s Ball,” etc.
Three Secrets of the Eastern Shore books are chock full of ideas for supper roadtripping, cool destinations, and one-of-a-kind attractions on the Delmarva Peninsula. You’ll find them at this link–two collections of Eastern Shore Road Trips as well as Shore Fun! The Delmarva Wanderer’s Guide.
The first Eastern Shore boat-docking contest of 2026 happens in Rock Hall, Md. Sun July 5. A dozen other contests on the Eastern Shore and a few on that other side of the Chesapeake as well. Info on the whole season.
The name is a mouthful, but I’ve been a couple time and it’s both interesting and fun. The Old-Time Wheat Threshing, Steam & Gas Engine Show returns on the weekend of Aug 7-9 along the backroads near Federalsburg, Md.
The Delaware State Fair in Harrington (July 23-Aug 1) is both big-ticket extravaganza and small-town joy. Headliners include Tracy Lawrence, Anne Wilson, Weird Al Yankovic, lots more. Demolition derby, harness racing. Be sure to have a corn dog or two while savoring old-time carnival midway joys.
The Groove City Culture Fest block party in Cambridge, Md. on Sat Aug 15 is a celebration of that town’s incredibly rich African American history. Fun theme this year: “Hip Hop vs Go-Go.” One headliner: DC go-go legends The Junk Yard Band. Lots of dancing and vendors and food and community joy.
It’s a big anniversary year for the Smith Island (Md.) Camp Meeting–the first of those prayer meetings was an astonishing 140 years ago. They’ll be gathering again July 26-Aug 2. All faith traditions and denominations welcome.
The name is a mouthful, but I’ve been a couple time and it’s both interesting and fun. The Old-Time Wheat Threshing, Steam & Gas Engine Show returns on the weekend of Aug 7-9 along the backroads near Federalsburg, Md.
The world famous Pony Swim in Chincoteague, Va. is Wed July 29, but it’s really a weeklong event with roundups and auctions and a carnival and lots more.
Caroline Summerfest in Denton, Md. Fri/Sat Aug 21/22. Car show, two stages of music, fireworks, a gazillion vendors, lots of food, street performers, more.
Head to the Maryland’s Upper Eastern Shore on Fri/Sat July 31/Aug 1 to celebrate Betterton Day(s) in a town that once ranked as a popular and storied beach resort. Friday fireworks and party, Saturday parade, crafts, food, vendors, and more, all centered around on the town’s historic beach.
The August Quarterly festival Wilmington, Del. is the nation’s oldest continuous celebration of black culture and faith, dating to 1814. Various events Aug. 23 to 30–with the big day being Sun Aug. 30 with gospel music, storytellers, food stands, children’s activities, and more in pretty little Tubman-Garrett Park.
