☀️ Happy First Day of Summer! Around here, we don’t let a season pass without squeezing every last drop of fun out of it—and summer on the Chesapeake Bay is nothing short of iconic. Whether you’re a local or just visiting, this is your definitive checklist for an unforgettable summer in Annapolis and Anne Arundel County. Think paddleboards, crabs, fireworks, and alfresco dining—with plenty of local flair and waterfront vibes.
So grab your sunhat, round up your crew, and see how many of these you can check off before Labor Day rolls in!
🚤 Your Chesapeake Bay Summer Bucket List
☑ Paddleboard the Severn River
Paddle along the peaceful shoreline of the Severn River, and if you're lucky, you’ll catch skates performing their graceful mating dance just below your board. Whether you're a seasoned paddler or just getting started, local outfitters like Capital SUP make it easy to get out on the water—with convenient rental locations throughout Annapolis and across Anne Arundel County, perfect for exploring hidden creeks, quiet coves, and scenic byways of the Bay.
☑ Watch a Severn River Sunset at The Severn Inn
Roll up by car or glide in by kayak to this beloved waterside gem perched on the edge of the Severn River—The Severn Inn. Settle in on the spacious deck and start with their signature crab dip, a Chesapeake classic that pairs perfectly with one of their local craft cocktails or a crisp glass of wine. From your table, you’ll have front-row seats to one of the most iconic views in Annapolis: the majestic domes and rooftops of the U.S. Naval Academy set against the golden hues of a Severn River sunset.
☑ Devour a Proper Crab Feast
It’s not summer until your hands are covered in Old Bay or JO (you choose, we won't judge!) Pick your own dozen at one of our favorite crab houses like The Point or Mike's, or cruise into Wild Country Seafood in Eastport for a fresh bushel of freshly caught Blue Crab beauties! Check out our dockside dining guide here for more waterfront dining across the region.
☑ Hit the Links for a Family Golf Outing
Dust off the clubs—Anne Arundel County is teed up for your next family outing. Whether you're perfecting your swing or introducing the kids to the game, the region offers a wide range of public and private golf courses suited for every skill level. From championship layouts with scenic fairways to a charming par-3 course that's ideal for quick rounds and younger players, there’s something for everyone. Spend a leisurely afternoon on the green, enjoy some friendly competition, and make memories that go far beyond the scorecard. Anne Arundel County Golf Guide
☑ Play Pickleball Under the Stars
It’s official—Annapolis is Pickleball-obsessed, and this summer’s lineup proves it. With new courts popping up across Anne Arundel County, from Truxtun Park to private clubs, the pickleball craze is serving up fun for all ages and skill levels. But the real star of the season? Pickleball Under the Stars—a one-of-a-kind experience that combines friendly competition with the magic of alfresco dining during Dinner Under the Stars on West Street every Wednesday night. Picture twinkling lights overhead, live music in the background, and pickleball paddles in hand. It’s as Annapolis as it gets. Want to join the fun? Reach out to the Annapolis Pickleball Club for details on how to play, volunteer, or simply cheer from the sidelines..
☑ Dine Alfresco at Dinner Under the Stars
On summer evenings, charming West Street transforms into a twinkle-lit, open-air dining destination every Wednesday and Saturday. Enjoy themed nights, live acoustic sets, and the unbeatable energy of Annapolis in full summer swing. Whether you're sipping cocktails under the string lights or catching a spontaneous street performance, this is a local favorite for a reason.
Pro tip: Tables fill up fast—make your reservation early and soak in the vibes! [Learn more here.]
☑ Celebrate July 4th in Historic Annapolis
America's smallest state capital (in square miles😀), Annapolis, has big connections when it comes to our storied revolutionary past. Party like it’s 1776 at the city’s annual July 4th Parade and fireworks show, where red, white, and blue light up the skies over Spa Creek and the harbor. Mark your calendars for 2026, when the U.S. celebrates its semiquincentennial (that’s our 250th birthday in layman’s terms!)—and Annapolis will be at the heart of the celebration. From colonial reenactments to patriotic pageantry, there’s no better place to salute America than in our historic capital, where cobblestone streets and waterfront views meet centuries of tradition.
☑ Set Sail—Literally!
No Chesapeake Bay summer is complete without getting out on the water.Whether you're craving a relaxing sunset sail aboard the iconic Schooner Woodwind or rallying your crew for a festive Naptown Tiki Cruise around Spa Creek and City Dock, Annapolis delivers. After all, they don’t call it “a drinking town with a sailing problem” for nothing. Want even more ideas? Head to the Visit Annapolis & Anne Arundel County website for a full lineup of boating, fishing, and sailing adventures across the region.
☑ Stroll the Anne Arundel County Farmers Market
Just off of Riva Road, pick up fresh local produce, artisan goodies, and coastal blooms at their weekly market. It’s a local tradition and the perfect morning activity before an afternoon on the water. Please note- four legged friends are not allowed, but for pet friendly fun across Anne Arundel County, visit our blog!
☑ Explore Quiet Waters Park by Kayak or Bike
From forested trails to gentle coves perfect for kayaking, Quiet Waters is a summertime favorite. Rent a bike or boat and explore this peaceful green space in the heart of Annapolis. Pets are welcome, and they even have a dog park and separate dog beach for bay frolicking! But don't stop there, Anne Arundel County has a wonderful network of state, county, and regional parks. Read our parks guide here!
☀️ Ready for Your Perfect Chesapeake Bay Retreat?
This list is just the beginning—life along the Chesapeake Bay offers endless ways to savor the season. From sun-soaked adventures to waterside traditions, there's no better place to call home.
Ready to immerse yourself in this idyllic setting? Discover your dream waterfront property today and start living the life you've always dreamed of, surrounded by the natural beauty, rich history, and unmatched lifestyle that only the Chesapeake Bay can offer. Let us help you make that dream a reality—contact the Brad Kappel Team today and take the first step toward living your best life on the Chesapeake.
