Travel by Region: Eastern Shore

Awesome Maryland Playgrounds Your Kids Will Love
Cross Island Trail
Paved Bike Trails on the Eastern Shore
Hyatt Regency Chesapeake Bay slide
Make a Splash on the Eastern Shore
Jane’s Island Beach
7 Secluded Eastern Shore Beaches Worth Exploring
The author’s son at Deal Island WMA in Somerset County, MD.
Hidden Hiking Trails on the Eastern Shore
Historic Saint Mary’s City Actor
Trips Inspired by Milestones in Maryland History
Autobahn Indoor Speedway in Jessup, MD
3 Road Trips to Take With Teenagers
Mandala Pies
A Guys’ Weekend in Berlin, Maryland
Birders squint into their binoculars to identify the members of a raft of ducks in a cove at Eastern Neck National Wildlife Refuge in Kent County, MD
An Exclusive Waterfowl Walk at Eastern Neck
Man receiving a facial at The Spa at Turf Valley
Treat Yourself and Book a Spa Day
Wist mountain coaster
Your Ultimate Guide to Winter Fun in Maryland
Carolers during Midnight Madness in Annapolis
Celebrate Midnight Madness in These 3 Downtowns
Immerse Yourself in Victorian London at Chestertown’s A Dickens of a Christmas
Liquid Asset’s Ice Cream Sammie
A Food-Filled Weekend in Worcester County
8 Things to Look Forward to at the 2022 Waterfowl Festival
The Ultimate Fall Foliage Road Trip
bbq spread
Dig Into These Kent Island Eats
7 Ways to Enjoy the Exciting Arts Scene in Kent County
sisters on a playground by the water
Pull Over! Playgrounds Right off the Road
two white Adirondack chairs
A Weekend of Romance On The Road
cowboy jumping through rope
Pair History With Fun at These Eastern Shore Destinations
couple enjoying wine
The True Love Story Behind Love Point Vineyards and Winery
mom and son in apple orchard
Pick, Sip, Shop: Where to Celebrate Maryland’s Fall Bounty
Author on ferry with motorcycle
Key Lime Pie Or Bust: My Motorcycle Drive to Mandala Pies
people playing on the beach at Deep Creek Lake
Find Your Dream Waterfront Vacation in Maryland
Assateague Outfitters kayak group near wild ponies
Summer Like the Locals on Assateague Island
two white Adirondack chairs
8 Ways to Feel Like You’re on [Kent] Island Time
Bas Rouge, plated food
Eat Your Way Through the Eastern Shore
Storefront of Earth Tones Cafe
5 Reasons to Drive to Denton, Maryland
Kayaking on Blackwater national wildlife refuge
Adventure and Romance on the Eastern Shore
Biking on the Millstream trail in Centreville, MD
Bike Rides and Blue Skies: Small Town Charm in Centreville, MD
Rocky Gap
Explore the Outdoors: 4 Must-Visit Maryland State Parks
The “Reel” Deal: Where to Go Fishing in Maryland in Winter
Let’s Go Shopping in Easton, MD
Chesapeake Bay Bridge
A Tale of Two Marylands: How the Chesapeake Bay Bridge United the Free State
A Winter Girls Weekend in Ocean City
Take the Long Way Around the Bay
Couple with wine by the water
Wyldly in Love: A Romantic Getaway to Wylder Hotel on Tilghman Island
Kids using duck calls
8 Things You Won’t Want to Miss at the Waterfowl Festival in Easton
Milkshake at Rayne's Reef Soda Fountain
From Milkshakes to Mermaids: 4 Things to Do in Berlin, MD
chestertown maryland
Charming Maritime Towns in Upper Eastern Shore
4 Underground Railroad Tours in MD That Spotlight the Bravery of Freedom Seekers
Father and Son look at the beach
48 Hours of Free-Roaming Family Fun in Upper Shore, Maryland
Boats in the water with the bridge in the background
48 Hours of Exploration in Charming Chesapeake City
“Sail Your Road” – Shardana Sailing Charters
Sailboats on the water
Log Canoe Sailboat Races: A Thrilling Chesapeake Tradition
A woman sitting on a boat overlooking the water
The Tale of the Sail: Finding Your Adventure on the Chesapeake Bay
Off the Beaten Path: Exploring Waterfront Villages on the Eastern Shore
Chestertown: A Charming Destination With Rich History on the Eastern Shore
Interior of the Mermaid Museum
Encounter Treasures Untold at the Mermaid Museum in Berlin, MD
The Chesapeake Bay Maritime Museum, courtesy of Shore Studios
Learn, Experience, and Taste the Legacy of Maryland’s Watermen
Femail wearing a black mask and beanie hat holding her enormous bloody mary beverage
A Weekend Away With a Dash of Old Bay: 3 Bloody Mary Stops in Ocean City
Gloria Richardson and protestors facing National Guard troops, Cambridge, Maryland, ca. 1963
Road Tripping Through Women’s History on the Eastern Shore
Man riding on a bike on the OCMD Boardwalk
Beachside Thrills Even During Atlantic Chills
A Mallard Hen In Flight, Captured at Oakley Street in Cambridge
Fowl Play on the Eastern Shore
People on a boat in the ocean
An Island Forged by Water and Tradition
Postcards from Cambridge
Adventure for One in Cambridge
Explore History and Heritage in Wicomico County
Animals, Ales, and the Outdoors in Wicomico County
Classic Cars in a Quaint Boating Town
Greyhound Bookstore Shelves
The Greyhound Bookstore: A Destination for Bibliophiles
Kitty Knight Outdoors
Fall Cocktails Along Maryland Route 213
The Inn at Perry Cabin
The Inn at Perry Cabin
All Experiences

Road Trips

Hyatt Regency Chesapeake Bay slide
Make a Splash on the Eastern Shore
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Sky lifts
Outdoor Attractions to Visit This Winter
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friends with cocktails
Sip and Savor Maryland Spirits
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All Road Trips