Seafaring families may already be dusting off their boats and setting their sights on the best spring weekend to get out on the water. If your family is seeking the watersport fun of the season, but with enough townie activities to keep you busy on the brisker days, try Annapolis, Maryland, on for size. April brings longer days for strolling through town, warmer weather for sailing and plenty of festivals to highlight the Anne Arundel County and Annapolis’s springy side.
First up, the Annapolis Book Festival is for all the readers in your family. The city welcomes nationally renowned authors for panel discussions and signings April 6, as well as big sales in local used bookstores. There will be live music and dancing, crafts for kids and family-friendly literary finds throughout the area.
If nautical fun is really all your family has time for, head to Maryland in time for the Wednesday Night Sailboat Races, April 24–Aug 28. Hosted weekly by the Annapolis Yacht Club, the annual event showcases around 130 crews racing through Chesapeake Bay. Even if you can’t fully sell the idea to your teens, try to stop by for a race or two while in the area — the Naval Base and surrounding waterways are worth a visit. Read more about the calendar lineup here and pick your favorite.
Speaking of boating, the Annapolis Spring Sailboat Show is now in its eighth year, hosted on the City Dock. Check out the lineup of nautical exhibits and surf shops, April 26–28, including nautical tech, boating gear, clothing and accessories.
If your family is new on the boating scene or your kids want to get into the family hobby, Boat Maryland Week kicks off April 26–May 5, offering fun and informative activities, including classes and exhibits for beginners. Noticing a theme here? You’re right — the inaugural week celebration coincides with the area’s beloved sailboat races, shows and fun events, sending a celebratory frenzy through the town.
In keeping with the spring-sailing fever, the Annapolis Cup Croquet Match is now on its 37th year, bringing a Gatsby-like party scene to the lawn, April 27. Dress the part and visit the green for some old-fashioned fun.
Finally, no festivity or seasonal celebration is complete without some food and drinks. This year marks the first Food and Spirits Festival of Annapolis, celebrated April 27–28. This lawn party brings foodie fun to the fairgrounds, including local brews, wine and live music. Load up on local cuisine with the kids, or pair with a beverage with the adult children — either way, it’s not a bad way to kick off the spring season.