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The region’s unique artistic style will take the spotlight when the Chesapeake Bay Maritime Museum hosts the Eastern Shore Sea Glass & Coastal Arts Festival on April 18-19.

The 8th annual St. Michaels Chocolate Fest returns on Saturday, March 7, 2026, from 11am to 4pm. Visitors can stroll through town and purchase tasting samples from over thirty participating businesses including limited-edition, chocolate-inspired dishes, desserts, and artisan confections.

The Blessing of the Fleet ceremony is an age-old tradition typically held in the Spring when watermen are preparing for the opening of a new season. Local watermen bring their boats to the harbor, and local clergy will gather together with the watermen’s community to pray for a blessing of safety and prosperity for the upcoming crab, clam and fishing seasons. They will also pray a blessing of safety for all those who pass through the waters of the Bay Hundred region during the recreational boating season. The blowing of the Shofar has become a tradition at the ceremony and the Bay Hundred Men will join us in song.

Easton will celebrate its community and Irish heritage once again during the Annual St. Patrick’s Day Parade on March 17th. The festivities include the parade at 5:30pm and the popular St. Patrick’s Day Potato Races right after the parade. Many businesses and organizations will decorate golf carts to show their Irish spirit and decorating skills. Judges will also vote for the Best Decorated Cart trophy.

The Easton EDC is thrilled to announce Chesapeake Fire & Ice, presented by Preston Automotive Group, a two-day spectacular family-friendly ice carving festival on Friday, February 20th & Saturday, February 21st, 2026.

Celebrate Valentine’s Day and support the work of the St. Michaels Community Center, the heart of our community, as the Julie Parsons Project Jazz Trio takes the floor at the St. Michaels Community Center (SMCC) on Friday, February 13 at 7:00pm. With their silky smooth vocals and remarkable artistry, the trio effortlessly blends classic jazz traditions with modern sophistication, delivering a performance filled with romance and tireless melodies. This special performance will transform the lobby of the Center into an intimate cabaret setting where you will enjoy not only the mesmerizing sounds of the Julie Parsons Trio but also delight in sweet and savory nibbles prepared by the Center’s own Chef Michael paired with sips of sparkling wine.

For All Seasons is hosting an online Valentine’s Day Silent Auction from February 5 to12, featuring extraordinary experiences and unique getaways – the perfect way to find a meaningful gift just in time for Valentine’s Day!