Cambridge Classic Power Boat Regatta
May 15th, 8 a.m.; Renditions Golf Club, Davidsonville
Join us for a great day of "Golf Fore Our Girls" while benefitting Girls on the Run of the Greater Chesapeake girls, ensuring access to our positive, youth development program across our region. Enjoy 18 holes of golf, on-course refreshments and a Taste of Mexico taco bar lunch, closest to the pin contests, happy hour, prizes and FUN. Please reach out to information@gotrchesapeake.org if you're interested in sponsoring the tournament.
May 15th, 6 p.m.; Fluegel Alumni Center, Annapolis
Join your Friends for a fabulous Night Out to support The Light House, a homeless prevention support center. USNA Fluegel Alumni Center provides a spectacular location overlooking College Creek! live music • light fare • full open bar
May 16th through 18th; Oxford Community Center, Oxford
Located on Maryland’s pristine Eastern Shore, the Oxford Community Center’s annual three-day Fine Arts Show ushers in the summer season for the local arts community. The juried exhibit draws a wide selection of collectors from the local area as well as from the Baltimore-Washington, Philadelphia, Virginia and New York City arenas and has been a highlight for several decades.
May 17th; St. Michaels High School
This race is one of only two Maryland events recognized in the TOP 100 HALF MARATHONS IN THE USA! Our course is built to help you reach a new PR. The first mile takes you through downtown St. Michaels – one of the most picturesque waterfront towns in the region. Once you pass Talbot Street you will run through waterfront communities and down country lanes as you wind your way back towards the downtown area for the finish line celebration. Strollers are not permitted in the half marathon.
Cambridge Classic Power Boat Regatta
May 17th through 18th; Cambridge
The oldest active powerboat race in the country happens right here in Dorchester County, Maryland. This year's race will be held on May 17-18, 2025 on the Choptank River. About 70 boats are expected to be on hand to create an exciting two days of racing. Admission is FREE with a $5 a day donation for parking. Kid's Zone, food, and drinks will be available.
3rd Annual Fairy House Festival
May 17th through June 22nd; Quiet Waters Park, Annapolis
Fairy Houses will appear along the Holly Pavilion Trail beginning on Saturday, May 17th and the Opening Fairy House Festival Enchantment will begin at 2pm that day! Costumes are welcome at the celebration and anytime thereafter.
May 19th; Queenstown Harbor Golf Course, Queenstown
Bo's Effort seeks to assemble community resources to break the stigma of mental illness through education and guidance. We look to fund initiatives that offer awareness to families and individuals seeking to manage their illnesses and live healthy and productive lives. Our cause is a big one. We want to make a difference in mental health and ask for your support for families in our community.
Commissioning Week Blue Angels Air Show
May 21st and 23rd; Annapolis
The United States Naval Academy Commissioning Week is a celebration for Midshipmen, their families, and the entire town of Annapolis. Woven into the fabric of our historic city, visitors come from all over to celebrate this special honor with graduating Midshipmen.
May 24th and 25th; Maryland Zoo, Baltimore
Celebrate Memorial Day weekend at Baltimore’s wildest beer festival! Enjoy your favorite craft brews while wandering through the Zoo and encountering incredible animals, all in support of our largest fundraiser of the year. With so much excitement planned, this is an event you won’t want to miss! Plus, every ticket supports animal care and wildlife conservation efforts.
May 23rd to 25th; Downtown Chestertown
In response to British Parliament’s closing of the port of Boston, the citizens of Chestertown, Maryland met in May of 1774 and set forth “Resolves” forbidding importing, selling, or consuming tea in Chestertown. According to local legend, residents then gathered at the town center, marched down High Street to the brigantine Geddes, which was anchored in the Chester River, and tossed her cargo of tea overboard. The annual reenactment of that event is the centerpiece of the Chestertown Tea Party Festival. The re-enactment is scheduled for 2:00 p.m. All Festival events take place along the Chester River and in the historic district of 18th-century Chestertown, Maryland. There is no admission charge to the Festival.
Rock Kent: Jimmy and the Parrots - A Jimmy Buffett Tribute
May 22nd, 7 p.m.; Kent Island Resort
Get ready for a tropical escape with Jimmy and the Parrots, the ultimate Jimmy Buffett tribute band! 🌴🎶 Join us at The Beach Bar on Thursday, May 22, 2024, from 7 PM to 8:30 PM for a night of island vibes, classic tunes, and laid-back fun as we pay tribute to the legendary Jimmy Buffett.
