Plan Your Visit
Spring is coming to the Chesapeake Bay, which means longer days, warmer temperatures and dozens of boat shows, festivals, exhibitions, and expos! Do you enjoy hard or soft shell crabs, craft beer, homegrown wine, baseball, or the blues? Chances are you’ll find it in a quaint, coastal town, just a short boat ride away from Herring Bay. Here are a few fun suggestions!
March 7-8, 2020
St. Michaels ChocolateFest/ChocolateFest Crawl
St. Michaels, MD
If you didn’t get enough chocolatey deliciousness (can you ever really get enough?!) over Valentine’s Day, then you’re in luck! At this annual 2-day event, you’ll find some of the most decadent cocoa confections ever. Maryland’s most talented chefs create them. Pair your chocolates with locally, hand-crafted beer and wine.
April 4-5, 2020
Eastern Shore Sea Glass and Coastal Arts Festival
St. Michaels, MD
This annual 2-day waterfront event has it all! Seminars on the fascinating history, or sea glass, dozens of local artisans specializing in beautiful, hand-crafted jewelry, unique art, photography, and one-of-a-kind, coastal, home décor, locally crafted beer and two stages showcasing some of Maryland’s best musicians!
April 17-19, 2020
Bay Bridge Boat Show
Celebrate the Spring boat show season at this annual 2-day event! This show is fun for the entire family! Explore more than 400 powerboats on display, or attend one of the many seminars and in-water training courses. Kid-friendly activities, raffles, and local food and beer vendors will be on hand.
April 24-26, 2020
Annapolis Spring Sailboat Show
Explore the beautiful Annapolis waterfront, browse and board the latest and greatest sailing vessels, chat with dozens of vendors and exhibitors, attend one of the educational seminars and workshops, sample tasty local food and drink offerings and enjoy some of the best local live entertainment.
May 2-3, 2020
Lower Bay Boat Show
This annual 2-day show, located just off the ICW, in the lower portion of the Chesapeake Bay, boasts over 80 new and pre-owned boats on display, an array of cool tech gear, clothing, and art vendors, and several delicious homegrown foods and beer offerings.
May 8-9, 2020
Deltaville Seafood Festival
What’s better than small-town baseball in May? Small town baseball, a waterfront seafood festival, a lip-synching contest, dozens of regional artisans, and live music from talented, local entertainers! You’ll find all this and more at this annual 2-day, family-friendly festival in Deltaville, Virginia.
May 15-16, 2020
Chesapeake Bay Blues Festival
Sandy Point State Park, Annapolis, MD
Head to the beautiful Western Shore of the Chesapeake Bay for this annual 2-day music festival! With the majestic Bay Bridge as your backdrop, you’ll groove out to some of the most legendary names in Blues, including The Spinners, Blues Traveler, Buddy Guy, and Shemkia Copeland. Local food and beverage vendors will make your experience that much cooler!
May 28, 2020
Soft Shell Spring Fair
If you’re a fan of Soft-Shell Crabs and a good time, you won’t want to miss this afternoon on the City Dock in the Eastern Shore town of Crisfield! You’ll enjoy crabs, locally crafted beer, arts and crafts, games, live entertainment, and the Waterman of the Year Awards.
May 30, 2020
St. Michaels BrewFest
St. Michaels, MD
This lively annual event features delicious local cuisine, live music from 13 local bands, and over 100 beers from local, regional, and national breweries, including seasonals, specialties, and collaborations!
May 29-31, 2020
Ocean City Sportsman Expo
Ocean City, MD
Head down the shore Hun for a weekend of fun-in-the-sun at this second annual 2-day expo! Here you’ll find experts on local wildlife, waterfowl, and conservation. Visit one of the many vendors who specialize in fishing, hunting, boating, camping, grilling, and everything outdoors.
Climb aboard, cast off, and discover all that the local Bay area has to offer!