Maryland Official Visitors Guide - 2026 Maryland Official Visitors Guide
Great Chesapeake Bay Loop Getaways
2025-11-04 05:30:21
Immerse yourself in this unparalleled universe as you explore quaint waterfront communities along the loop and set out on excursions with Chesapeake Bay Storytellers.
Kayaks and Culture
Take a boat ride with Experience Smith Island to learn the waterman’s way of life and savor the Bay’s natural beauty. Special excursions include Smith Island Cake-making demonstrations. (More on p. 11) Across the Tangier Sound in Crisfield, unplug in cozy cabins at Janes Island State Park. Here, you can paddle miles of peaceful water trails to catch golden-hour sunsets and glimpse wildlife.
For a truly unique boat tour, cruise the Chesapeake & Delaware Canal with Chesapeake Water Tours. The Chesapeake City group will have you on the edge of your seat with tales of traders, explorers and freedom seekers who traveled this still-active shipping lane.
For a paddle trip that’s sure to please, pack your binoculars and launch into nature at Grasonville’s Chesapeake Bay Environmental Center — ospreys, eagles and otters wait to be spotted.
Come Sail Away
Let the Pride of Baltimore II take you on a guided tour as she cuts through the waves on a historical maritime adventure. Keep an eye on her schedule to see where in Maryland she’s sailing from when.
On Wednesday nights, make new mates at Annapolis Maritime Museum’s sailboat-race watch parties. Purchase tickets to get in on the action with complimentary cocktails and color commentary.
After the races, drift off in nautical style at Annapolis’ Graduate Hotel to rest up for a day touring the U.S. Naval Academy. Stroll the Yard to see historical buildings, explore exhibits and learn about the lives of midshipmen at the second-oldest of five United States service academies. More on p. 77
Keep your sea legs strong with day trips, sunset sails, weekend getaways and extended vacation charters aboard Shardana — a 43-foot sloop that sails out of Rock Hall.
Family Fun in the Chesapeake Sun
Spiral down the High Paw Holler, ride the “rapids” on the Chesapeake Plunge or spend a few days in a cabin-themed family suite and try it all at the Great Wolf Lodge in Perryville.
From wandering nature trails to feeding cute critters, Abingdon’s Anita C. Leight Estuary Center has yearround family fun to keep your little ones entertained.
Begin your Cross Island Trail trek at Terrapin Nature Park in Stevensville to hunt for sea glass and get oooh-worthy views of the Bay Bridge. Need wheels? Download the Fin Outdoor Recreation app and get rollin’ with bike rentals.
Based in Port Republic, Megalodon Adventure Charters takes you hunting for fossils, cruising to see frolicking dolphins, or paddling secluded shallows to hidden Bay beaches.
Bay Beach Bliss
Known for its gorgeous sunsets, Stevensville’s Matapeake Beach is the place to go for beach and pool swims and hikes sweetened by Bay breezes.
In addition to water fun, Point Lookout Swimming Beach in Scotland brims with Civil War history, stunning views of Point Lookout Lighthouse and a perch for some of the best bird-watching on the Potomac. More on p. 60
Take a dip, relax on the beach, walk the pier and boardwalk, or shop in family-friendly North Beach.
Once a popular resort town, Betterton Beach now boasts a sandy shoreline, a park, a fishing jetty, a boardwalk and gentle waves for leisurely swimming.
What is a Chesapeake Bay Storyteller? Known for being engaging and knowledgeable guides, Storytellers have received certification from the Maryland Office of Tourism and the U.S. National Park Service.
Find more ideas for your Bay getaway.
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