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Summer is here, and it’s time to soak up the sun, visit bustling beaches, learn about boating history and relish the small-town charm around the Chesapeake Bay. Read on for hidden gems and tried-and-true events along the Bay, all the way from Havre de Grace to Cape Charles. Whether you’re a fan of watersports, arts and crafts, street festivals, or coastal cuisine, you’ll find something worth docking for a while.
Yorktown Market Days, Fun in the Sun Market
Yorktown, VA
July 16 - Fun in the Sun Market;
August 6 - National Farmers Market Week
Experience a coastal Hampton Roads market on the York River. Check out local produce, meats, seafood, gourmet dog treats, art and more every Saturday this summer, and stop by one of the dates above for a themed, family-friendly extended market.
Where to Dock: Riverwalk Landing
Havre de Grace, MD
July 2
Enjoy this beautiful town through a mid-century Americana lens at the Independence Day festival. You won’t want to miss the Patriotic Pooch contest, 50s throwback entertainers and best of all, derby races on Pennington Avenue.
Where to Dock: Tidewater Marina
Sea Glass & Beach Crafts Market at Annmarie
Solomons, MD
July 2
Kick off the holiday weekend at the Annmarie Sculpture Garden & Arts Center’s annual beach-themed market. Browse all things crafty and sea glass at over 50 booths!
Where to Dock: Solomons Harbor Marina
Rock Hall, MD
July 3
For the first time since 2019, stop by and celebrate watermen who dedicate their lives to working on the Chesapeake! Enjoy a day of family fun, including anchor tosses and a raffle, culminating in the infamous boat docking.
Where to Dock: Haven Harbor Marina Resorts
Tuckahoe Steam & Gas Association’s 49th Annual Show
Easton, MD
July 7-10
Calling all car, truck and train enthusiasts! This multi-day show will be packed with steam and gas engines; antique tractors, trucks and cars; live steam train models; and even a horse pull.
Where to Dock: Easton Point Marina
Annapolis, MD
July 9
Sponsored by the Eastport Yacht Club, this open water race has something for all levels. Experienced paddlers can fight it out in the seven-mile Challenge, and recreational paddlers will enjoy the 3.5-mile Challenge or one-mile Just for Fun race.
Where to Dock: Eastport Yacht Center
Easton, MD
July 17-24
Plein air painters express their craft from life instead of the studio, so you’ll see artists from across the country painting all around town. Also attend lectures and workshops, and buy art and other goods downtown all week.
Where to Dock: Easton Point Marina
Hampton, VA
July 23
Dock at the transient slips in downtown Hampton, then join the landlubbers at Langley Speedway, one of NASCAR’s best weekly tracks, for the annual Hampton Heat races.
Where to Dock: Bluewater Yachting Center
Southern Maryland Boat Club Bash on the Bay
Leonardtown, MD
July 29-31
Since the Calvert Marine Museum opened an exhibit on the golden era of powerboat racing in 2013, this vintage boat club has put on several races a year. Make your way to the historic Leonardtown Wharf to see vintage powerboats in action.
Where to Dock: Combs Creek Marina
July 30
Annapolis, MD
Things are sure to heat up at the fourth of five tournaments in the 2022 Snakehead Championship Series at Anglers Sport Center. Anglers in kayak/shoreline and boating divisions will be up for all kinds of prizes, including one from the Coastal Conservation Association Maryland’s Great Chesapeake Invasive Count.
Where to Dock: Podickory Point Marina
Annapolis Yacht Club Two Bridge Fiasco Race
Annapolis, MD
July 31
Cruise to the southern Chesapeake to witness this pursuit style race starting between the Chesapeake Bay Bridge and Severn River Bridge. Look out for all types of boats in the competition, and even a foiler or two if you’re lucky.
Where to Dock: Annapolis Yacht Club
Annual Chesapeake Bay Balloon Festival
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Cordova, MD
August 5-7
Embrace the Eastern Shore summer lifestyle at this family-friendly festival. Feel the adrenaline rush of hot air balloon rides and keep the thrill going on the mechanical bull and bouncy house on land.
Where to Dock: Easton Point Marina
A Day of Celebration & Remembrance of Harriet Tubman
Cambridge, MD
August 6
Celebrate Harriet Tubman’s life, bicentennial and antislavery activism on the Underground Railroad just miles from where she lived as a child. Join the commemorative parade through the streets of Cambridge and enjoy local vendors and entertainment at the festival.
Where to Dock: Cambridge Yacht Basin
Rock Hall, MD
August 12-14
Presented by Main Street Rock Hall, you can dock at a local bayfront marina ready for an immersive, family-friendly weekend. The whole family will love the marketplace on Main Street, pirate and mermaid performers, and costume contests, and there will be no shortage of grub and grog.
Where to Dock: Haven Harbor Marina Resorts
Solomons Dragon Boat Festival 2022
Solomons Island
August 13
Cruise to scenic Solomons Island to watch 30 dragon boat teams compete for glory on the Patuxent River and explore the local vendor village. Arrive the week before and you might catch a Dotting of the Eye Ceremony or even a flash mob.
Where to dock: Solomons Harbor Marina
Leo Wardrup Memorial Cape Charles Cup Regatta
Cape Charles, VA
August 20-21
Make your way to Virginia’s Eastern Shore for two days of racing on the Chesapeake. While you’re there, lounge on the Cape Charles town beach, stroll around the retail district and check out Victorian homes in the historic district.
Where to Dock: Cape Charles Yacht Center & Marine Services
7th Annual Coastal Craft Beer Festival
Virginia Beach, VA
August 27
Spend your Saturday at the waterfront Neptune’s Park, tasting your way through 60+ beers, ciders and seltzers from 30 breweries. Learn about all Virginia breweries have to offer or branch out with some regional or national craft brews.
Where to Dock: Rudee's Inlet Station Marina
Havre de Grace, MD
September 9-10
Cruise to the northern Bay to round out your summer with this annual festival, kicking off with a lighted boat parade. Enjoy fun for the whole family with fresh crab and seafood, beer gardens, live music, hot air balloons and a youth fishing derby!
Where to Dock: Tidewater Marina
2nd Annual Portsmouth Paddle Battle
Portsmouth, VA
September 10
Whether you kayak or paddleboard as a novice or a pro, or enjoy waterfront live music, food and drink, there’s a place for you in the Paddle Battle on the Elizabeth River. Proceeds will support the Portsmouth Naval Shipyard Museum and Lightship Portsmouth Museum.
Where to Dock: Tidewater Yacht Marina
Baltimore, MD
September 27-October 1
Close out your summer season with Passagemaker’s annual boat show held at Harbor East Marina in the heart of downtown Baltimore. The show hosts impression in-water selections of new and pre-owned long-rang cruisers, coastal cruisers and of course, tons of trawlers. Free seminars and educational demonstrations are held throughout the weekend.
Where to Dock: Harbor East Marina
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