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Charms of the Chesapeake--What to see on Maryland's Eastern Shore
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items Having lived in Easton for a number of years, I know some of the very best little spots! Pay a visit to St. Michaels, Cambridge, Chestertown and other places just over the Chesapeake Bay Bridge in Maryland. Here are the things to look for to make you...
Map
Sections
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Crab Cakes, Coffee and other Good Food
Where to Stay
Enjoying Nature
The Kids Will Love!
Museums and the Arts
Read all About Delmarva
Crab Cakes, Coffee and other Good Food
The food scene on the Eastern Shore is vast with a wide range of delicious and comfortable places to grab a bite or enjoy a gourmet meal.
The view over the water can't be beat, enjoy that while sipping delicious cream of crab soup. Afterwards, take a little stroll around town. Oxford is an absolute delight.
Doc's Sunset Grille - Oxford - Facebook
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Excellent casual eatery with a pleasant atmosphere and tasty pizza.
Ava's Pizzeria & Wine Bar
Super fun to sit outside at the ancient oak tables, under the gigantic sail cloth. Best mocha in Easton! And sometimes you can get a bite at the food truck located on site.
RISE UP COFFEE ROASTERS - SERVING A SIP OF THE ...
Brick oven pizza! I always get the Medjool Dates and White Cheddar Salad, and the Maitake Mushroom is great if you want to take your chances with the shishito peppers. Most are mild and about one out of ten are spicy. You never know what you are going to get. One of t...
Restaurant | Out of the Fire | Easton, MD
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I never managed to get to Caroline's when I lived quite near Denton, but I follow this Farm to Table restaurant on Facebook and it looks SO good!
Caroline's in Denton
Where to Stay
The Eastern Shore has everything from quaint rentals of small homes, to rentals of larger estates, and some world class hotels with spas and pretty grounds to explore.
Book yourself in to the historic Tidewater Inn and spend the afternoon walking around the charming town of Easton Maryland. Relax in the outdoor cafe at the Hunters Tavern
Easton's Historic Tidewater Inn
There are so many cute little houses in town, some dating from the 1600s. And it's a good place for biking around town.
VRBO sometimes has places in St. Michaels
Dawn a frette robe and head to the relaxation lounge with chaise lounges shaped to follow the body’s contours and padded to cradle in comfort. Then you are ready for your facial or Arnice deep tissue massage.
Terrasse Spa at the Tidewater Inn - The Tidewater Inn
Idyllic setting on the Miles River, complete with luxurious spa and history to the hilt. As featured in The Wedding Crashers.
Inn at Perry Cabin Resort | St. Michaels, Maryland
Enjoying Nature
Maryland's Eastern Shore still have plenty of unspoiled places for biking, hiking and watercraft.
I have seen snow geese by the thousands here in the winter, and so many bald eagles. There is a lovely loop drive through the refuge, good for biking as well as driving. There are several trails to walk and you can walk up the boardwalk over the marsh. At the right time of year you could see muskrats or at least their dens.
Blackwater National Wildlife Refuge | U.S. Fish & Wildlife Service
Protected swimming and a small sandy beach! Also walk on the bridge over the highway to access the fishing pier. This is the old route 50
Sailwinds Beach Park at Cambridge
Lovely area with a walking trail from visitors center to the beach. Walk left past the oyster shell midden to access one part of the beach, or go right and walk along the pine trees bordering the Chesapeake Bay. Blue Herons and other birds can be seen from the boardwalk and there are benches to sit on for a picnic or to watch the boats.
Ferry Point Park in Chester Maryland
Lovely walking trails and a nice gift shop in the visitor center where I've picked up gifts made on Maryland's Eastern Shore. You can hear frogs and maybe see them from the boardwalk over the pond.
Adkins Arboretum Botanical Garden
The Kids Will Love!
Playgrounds and sandy Chesapeake beaches for the kids. What's not to love?
Super fun shady zoo and no admission fee! The spider monkeys and the parrots are a scream and where else can you see capybaras and alpacas? This is a fun shady place, great for an afternoon activity.
Salisbury Zoo
You can save yourself a little bit of a drive if you are heading to St. Michaels after an afternoon strolling around Oxford. Cars, bikes and pedestrians alike can ride. For kids, it's a rare treat!
Oxford-Bellevue Ferry
Super fun playground for the kids, quite extensive and large. And don't miss the little playground, past the gazebo. There's an old boat and a small hill which tots delight in. Good walking path. A pretty fountain. A basketball court and a little fre...
Idlewild Park - Fun for Kids in Easton, MD
Sweet bookstore in the heart of Easton. I love the curated kids book selections…..and the kids love romping in the little play area. Great meeting spot!
Welcome | Flying Cloud Booksellers | Easton, MD Independent Bookshop
Museums and the Arts
Easton is home to a vibrant arts community.
Eighteen acres of waterfront with exhibits focusing on the bay and its people, with exhibits, activities and fireworks on the fourth of July. You can dock your own boat or your yacht (!) and have dinner just a short walk away. Or you can take a boat ride and get out in the Miles...
Chesapeake Bay Maritime Museum
The Underground Railroad is one of the most remarkable stories in American history. This is a story of ordinary men and women coming together in harmony, united to pursue the extraordinary mission of helping those in their journey to freedom. This mo...
Harriet Tubman Underground Railroad National Historical Park
Don't want to go home to bare walls? PIck up a painting by a local artist. Seaside scenes, nautical prints and oil paintings and waterfowl are favorites at several lovely galleries. Pictured is the Trippe Gallery in downtown Easton.
Local Art Galleries
Remember your trip to the Eastern Shore with a print from area photographer Sharon V. Lee. She does some gorgeous work! Pictured here, the drawbridge at Tilghman.
Nautical Photography Prints
The acoustics are excellent in this small venue. Some big names come here to play. I have seen Don McLean there. He looked right through me as though I wasn't there, as they say. And he sang American Pie. Super fun was a performance of Ladysmith Black Mombazo.
Avalon Theatre
The Treasure Chest is tied for First Place as the Best Unique Gift Store on the Eastern Shore for 2025, as voted by What’s Up? Magazine. It's a sweet little spot in the lovely waterside town of Oxford. You should go!
Treasure Chest in Oxford MD
Read all About Delmarva
I always prepare for a trip by reading about the destination. Here you can dig into some deep info or try a few short stories.
When I moved to Easton I started reading the quintessential historical novel about the region. James Michener moved to St. Michaels and lived there for a year or two and interviewed the locals and researched the history to write Chesapeake: A Novel. ...
Chesapeake: A Novel
Hysterically funny stories, all set in a gated home community on Maryland Eastern Shore. John Barth grew up in a house near the Choptank River in Cambridge, Maryland, where his father operated the local soda fountain; he began his literary career by writing for the school newspaper at Cambridge High School. After a storied career Barth lived in Chestertown and was surely writing about life there, but as I read it, I was pretty sure it could have been right down the road from where I lived on the Frederick Douglass Highway in Easton.
The Development
While I have not read this book, yet, I have observed the subsidence of the land on the Eastern Shore, both at Blackwater WNR and at Hooper's Island. I had friends who moved off of Taylors Island because they were tired of wading through water to get...
The Disappearing Islands of the Chesapeake
This book changed how I see a garden. It can be made to feed the creatures, or it can just be for beauty. Barbara Ellis details steps we can take to make our gardens and landscapes more eco-friendly. Very helpful for gardeners in the Mid Atlantic reg...
Chesapeake Gardening & Landscaping Guide
Festivals and Events
Come at certain times of the year and enjoy one of the Eastern Shores fun festivals.
All kinds of fun on a winter day. Dog races in the water. Duck calling. Duck decoys and more at the Vendor tents, but the best is the Oyster Soup. Also an art show featuring favorite local artists of the Chesapeake and Delmarva regions.
Waterfowl Festival Easton Maryland
One of the largest annual tall ship gatherings in North America: a long-weekend of Tall Ship sails, tours, live bluegrass music, lectures, exhibits, family activities, regional food and more.
Downrigging - Main Street Chestertown
Join in the arts activities all week long. Art shows. Art lessons. Watch painters at their craft, as they set up on the picturesque scenes of the quaint town of Easton which dates from the earliest days of Maryland's history.
Plein Air Easton
I never managed to attend this but always wanted to go. The sea makes beautiful things out of glass that falls in the water. If jewelry is your thing, you can find gorgeous items here.
Eastern Shore Sea Glass & Coastal Arts Festival