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Happy new year! Here is a little help for you as you plan ahead to live up to that 2023 resolution. You know, to take more time to enjoy life, to get out and wander more often, to seek out fun adventures close to home. Do you have your calendar ready?

The Outdoor Show in Dorchester County, Md., Feb. 24 and 25 (with bonus event)

This affair may unfold in the middle of marshland nowhere below Cambridge, Md., but its reach is global. The World Championships of Muskrat Skinning will be decided in a middle-school gymnasium on the Saturday night of this weekend. Lots more leading up to that–a Miss Outdoors pageant, a slew of vendors, and an array of outdoorsy demos and competitions. Here is info.

Bonus: On Sunday the 26th–it’s the unforgettable Crawfish Boil and Muskrat Leg-Eating World Chamionship afterparty in Cambridge. Yes, the event delivers on that title. Great music, too.

The Great Delaware Kite Festival near Lewes, Del., April 7

Start your Easter weekend off right on Good Friday by heading to Cape Henlopen State Park near Lewes, Del. for what just might be the oldest kite festival in the country. It’s not just about kite-flying acrobatics. There is a humongous Easter Egg Hunt. A certain celebrity bunny will be in the house. Lots more, too. The 2023 details aren’t up yet, but here is a listing for last year’s event.

Eastern Shore of Virginia House & Garden Tour–Sat., April 22

Year in and year out, the Eastern Shore of Virginia Garden Tour ranks among the most popular tours of Virginia Garden Week. Around here, it’s a welcome-back-springtime excuse to wander the backroads while stopping at historic homes and strolling through gorgeous gardens. The itinerary varies from year to year, but it always includes Eyre Hall down near Machipongo–don’t skip out on that stop!  Details.

Ocean City (Md.) Springfest, May 4 to 7 (with bonus event)

Speaking of harbingers of spring, this will be the 32nd time around for the four-day Springfest bash in Ocean City, Md. Food, music, and artsy-craftsy shopping galore in the inlet area, with all the joys of the boardwalk just a short stroll away. Here is info.

If you want to double your fun on the Saturday of Springfest weekend (May 6), head to nearby Berlin to wander that town’s adorable old Main Street during the big Jazz, Blues, Wine, and Brews block party. Here is info.

Three Memorial Day Weekend Choices

Art and Music on Farm in Machipongo, Va. on May 27
Enjoy gospel, folk, bluegrass, and other roots music in the great outdoors on the gorgeous, historic grounds of the Barrier Islands Center museum. Some musicians will probably give workshops and demos. On top of all the music, fortysome top regional artists will be showing off their work. Here is info.

The Tea Party in Chestertown, Md., May 26 to 28
This colonial-flavored block party on Maryland’s Upper Eastern Shore is chock full of fun—a big parade, strolling musicians, lots of street theater, storytelling, guided tours, music, and more. It’s all set along the waterfront and downtown streets of a sweet town chock full of colonial history and architecture. Here is info.

Pirate Party Buccaneer BashThe Buccaneer Bash in Bowers Beach, Del., May 27 and 28
Brigands and lost treasure and bar fights! That’s the way things go at this Memorial Day weekend pirate bash. A Pirate wedding, too, and scavenger hunts, salty music, and salty language. You get the idea–maybe start planning your outfit sooner rather than later? The 2023 event listing isn’t up yet, but here is info from last year.

Plein Air Easton in Easton, Md., July 14 to 23

In one of the most prestigious events of its kind, top open-air painters from around the country do their best to capture the scenic and cultural wonders of our Eastern Shore while taking part in a weeklong run of talks, demos, and high-powered art sales events. One highlight: During the Quick Draw competition, 200 artists set up on downtown streets, looking to start and finish paintings in just two hours, with spectators (like you) milling about and looking over their shoulders. Here is info.

Chincoteague (Va.) Pony Swim & Auction, July 26-27

Have you crossed this one off your bucket list, yet? This famous affair occupies a spot on that list for countless folks with fond memories of reading the “Misty of Chincoteague” books as children. The Wednesday-Thursday swim-auction combo come smack dab in the middle of a week that’s chock full of other pony activities and things to do around the island. Here is info.
Word of advice: If you’ll need lodging or have your heart set on a spot with a view of the swim, start nailing down the details now.

Blessing of the Combines Snow HillBlessing of Combines in Snow Hill, Md., Aug. 5

Celebrate our agricultural traditions and honor our farming families at this all-American small-town classic, which kicks off with a parade of humongous, brightly colored farm vehicles rumbling through a downtown full of folks waving little flags and cheering our farmers on. The somber blessing follows. After that, it’s time for a big ol’ block party. The 2023 details aren’t up yet, but here is a Facebook page here is a website where they will appear soon enough.

Maryland Folk Festival at Salisbury, Sept. 23 and 24

Gospel, bluegrass, blues, go-go, Tlingit, Hawaiian, Nepalese, tejano, zydeco, Appalachian, yodeling, Hindustani–those were the highlights at last year’s rendition of this event. The 2023 lineup will likely be just as impressive. Plus, fun street performers and lots of showcasing of traditional Delmarva arts and crafts. Here is info.

Apple Scrapple Festival in Bridgeville, Del. on Oct. 13 and 14, 2023

Towns all over this land look for ways to celebrate their unique heritage and charms, but not many come up with ideas as close to pure genius as the people of Bridgeville, Del. devised back in the 1990s. The mid-October Apple Scrapple festival celebrates two pillars of the local economy–expect scrapple slings, skillet tosses, cooking contests & demos, car shows, a street dance, and scads of vendors. No 2023 details have been posted yet, but they’ll appear soon on this website and on this Facebook page.

Happy 2023 wandering!

–Posted by Jim Duffy for Whimbrel Creations LLC/Secrets of the Eastern Shore on Jan. 1, 2023.


  • Judy Martin says:

    Thanks for highlighting our event. I have put this year’s Buccaneer Bash information on our Facebook page.
    If you visit this year, look for me. I’d like to thank you for your support of the museum.

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