The Eastern Shore of Maryland is a lot bigger than most people realize. If you are coming from the Annapolis side of the Chesapeake Bay Bridge, it’s likely you will make a bee line for the ocean. However, there are so many hidden (and not so hidden) gems sprinkled all over the rest of the Eastern Shore too! If you want to plan an Eastern Shore day trip or weekend trip for your family but not necessarily go to Ocean City, check out these ideas for the best things to do on the Eastern Shore with kids!
For the purposes of this guide, we are defining Maryland’s Eastern Shore as Kent, Queen Anne’s, Caroline, Worcester, Talbot, Dorchester, Wicomico, and Somerset Counties. The Maryland Department of Tourism also includes Cecil County, but since it’s pretty easy to get to Cecil County without going over the Bay Bridge, we are leaving it out of this guide. Don’t worry Cecil County… we will cover you in another guide!
Go to a beach (not that beach)
Yes, you can definitely drive all the way to the Atlantic Ocean. Ocean City is quite awesome. But there are sooooo many other beautiful beaches along the way that are likely just as nice, but a lot less crowded. And the great thing about the Eastern Shore is that all the beaches on this list are free for public access. These are our top picks for a great Eastern Shore beach! And you can swim at all of the beaches listed. A beach trip is literally the most iconic outdoor adventure!
Matapeake Beach and Clubhouse
Located on the Chesapeake Bay on Kent Island, Maryland, the Matapeake Beach grounds include a public swimming beach, an outdoor amphitheater, family picnic area and 1 mile trail through the surrounding woods, with views of the Bay Bridge. The beach is open sunrise to sunset daily.
This lovely beach in Kent County used to be the center of a resort area. The sand is fine, the beach is wide, and because of it’s location at the mouth of the Sassafras River, there are no jellyfish!
Ferry Park Beach
This is the community park beach at Rock Hall, MD. This is a small beach with great views of the Chesapeake Bay.
The Strand Beach
Located in Oxford, MD, the Strand Beach is next to the Oxford-Bellevue ferry and it’s within walking distance of great ice cream at the Scottish Highland Creamery and the fun Bellevue Playground.
Deale Island Beach
To get to this hidden beach, turn right at the Deale Island boat marina once you cross over the bridge. The sand at this beach is very fine with a gentle slope into the water.
Roaring Point Park
Another hidden beach in Wicomico County is Roaring Point Park. You have to work for this beach but it’s sooo worth the effort. Pack a picnic lunch and head out to Nanticoke for a relaxing afternoon!
Visit a Family Farm
The Eastern Shore has some absolutely lovely seasonal farms that offer everything from pick your own fruits and vegetables, sunflower fields, pumpkin patches, and more! Here are our best picks!
There are so many reasons to visit Lockbriar Farms– pick your own fruit and flowers, sunflower fields, pumpkin picking, a corn maze, and ice cream from Lockbriar & Daughters ice cream stand!
Emily’s Produce in Cambridge, MD is a fantastic family run farm. They offer pick your own fruit, sunflower fields, and fall harvest activities.
This sweet little farm and creamery in Cordova, MD also serves Vanderwende’s Ice Cream (a fantastic creamery located just over the state line in Delaware). In the fall Councell Farms has pumpkin picking and a Field of Fun with 20+ farm related activities including a corn maze, jumping pillow, slides, and more!
Best Eastern Shore Playgrounds
Playgrounds are the perfect place to let kids burn energy on any day trip. There are fantastic playgrounds that will give your kids a great time! Here are our top picks:
- Idlewild Playground in Easton, MD
- Rock Hall Community Playground
- Betterton Community Park
- Manklin Meadows Park in Ocean Pines
- White Horse Park in Ocean Pines
- Tuckahoe State Park Tire Playground
- Ben’s Red Swings in Salisbury, MD
- Sailwinds Park in Cambridge, MD
- Stephen Decatur Park in Berlin, MD
- Northside Park in Ocean City
- Wilmer Park Playground in Chestertown, MD
Indulge in a Scoop!
There are soooo many fantastic places to get a scoop of ice cream on the Eastern Shore. These are our top picks!
- Island Creamery in Salisbury, MD and Berlin, MD
- Justine’s in St. Michaels, MD and Ocean City
- Bonheur Ice Cream in Easton, MD
- Storm and Daughters Ice Cream in Easton, MD
- Scottish Island Creamery in Oxford, MD (also served at Emily’s Produce)
- The FREEZE in Chestertown, MD
- Get the Scoop in Rock Hall, MD
- Dumsers Dairyland at multiple locations in Ocean City
- Kohr Brothers in Ocean City
- Ice cream at all the farms!
National Wildlife Refuges
A really fun way to explore the great outdoors with the whole family is to visit one of Maryland’s numerous national wildlife refuges. Here are the three best bets we recommend.
Eastern Neck Wildlife Refuge
Eastern Neck National Wildlife Refuge is a 2,285 acre island. The refuge holds the designation of Important Bird Areas by the Audubon Society. Over 240 bird species visit the refuge along with small mammals and many other wildlife species. There are fantastic views of the Chester River and Chesapeake Bay with 7 different trails. When we visited we saw bald eagles flying over the bay!
Blackwater National Wildlife Refuge
The Blackwater National Wildlife Refuge is a fantastic natural place to visit with kids. In the Winter months it is home to osprey, and throughout the year you can see bald eagles, turtles, and more!
There is an auto driving tour– The Wildlife Drive– and a few hiking trails. The Marsh Edge Trail is 1/3 mile long. The Key Wallace Hiking Trail is a 2.8 mile loop trail through the forest. The Tubman Road Trail isa 2.2 mile out and back trail. This trail can get pretty muddy so wear boots!
Terrapin Nature Park
Terrapin Nature Park is a 276 acre park with a 3.25 mile walking trail that runs through wetlands, flower fields, and a sandy shore line. You can’t swim at this beach but your kids will love playing in the sand, splashing (not swimming) in the beach side surf, and more! This park has a wheelchair-accessible boardwalk as well!
Hang Out On A Small Town Main Street
The Eastern Shore has quite a few quaint small towns where you can find fun things to do with kids or even as a romantic getaway or Mom-only trip! Here are some ideas to get you started!
Berlin is such a cute town it has been the backdrop for movies like The Runaway Bride. Berlin’s Main Street is full of public art, locally-owned shops, and great places to grab a bite to eat!
Easton has a vibrant art scene and a tons of award winning restaurants. Check out the Academy Art Museum or the Talbot Historical Society. If you want a hands on experience with your kids, drop into Kiln Born Creations and paint some pottery.
St. Michael’s is such a romantic and charming town. It’s right on the water and you can take a sailing cruise. Go on the self guided walking tour and duck into one of the many coffee shops and gourmet cafes for lunch!
Chestertown has a fantastic historical society and offers numerous events to celebrate that rich history throughout the year. It’s on the Crab and Oyster Trail and has an amazing seasonal Farmer’s Market.
Dive into the Chesapeake Heritage
Wow, there are so many ways to learn about the maritime history of the Chesapeake Bay. Here are some of the not-to-miss sites, historic areas, and museums, including a special museum for kids!
DelMarVa Discovery Center
The Delmarva Discovery Museum in Pocomoke City, MD is the best children’s museum in Maryland you probably haven’t heard of. There. I said it.
But really, this Museum is such a hidden gem… you absolutely should make time to visit. It’s about 45 minutes from Ocean City and only 30 minutes from Assateague! That makes it the perfect side trip .. and especially a great rainy day activity if you are at the beach!
Yes, there is a huge steamboat kids can climb in and around. Also, there are smaller boats kids can climb in, as well as a giant beaver dam, and a replica of the type of home Native Americans would have lived in!
Chesapeake Bay Maritime Museum
The Chesapeake Bay Maritime Museum is a great destination for kids and families. You can climb up into a lighthouse, explore exhibits in the working shipyard. Dip into the Small Boat Shed to see a number of boats, including a few log canoes adapted as used by Native Americans.
In the Maryland Crab Meat Company Exhibit you can see how crabs are actually harvested, and there is a great exhibit on oystering in the bay as well. In summer months visitors can try their hand at seeing if there are any crabs or oysters in the cages.
Deale Island Historic District and Skipjack Heritage Museum
Drive to the end of the island to see the harbor where fishermen still pull in crabs from the Chesapeake. While you are there grab a bite to eat at Arby’s Dockside… it’s the only restaurant on the island and the food is pretty great!
While you are there, visit the Skipjack Heritage Museum! This is a small museum dedicated to the history and story behind the Skipjack, American’s oldest working sailing vessel.
Furnace Town Historic Site
This is a fantastic living history museum right outside of Ocean City and one of the best historic sites in Maryalnd. The site sits on twenty-five acres of Furnace Town Historic Site, the 19th century village of the Nassawango Iron Furnace. You can visit the village recreation and tour buildings such as the Blacksmith building, Broom House, Farm Implement Building, one room schoolhouse, church, iron furnace and more.
Ocean City Life Saving Station Museum
The Ocean City Life Saving Station Museum is a museum dedicated to collecting and preserving the history of life saving on the Eastern Shore of Maryland, Delaware and Virginia. There are quite a few hands on exhibits (including touch tanks) perfect for kids!
Civil Rights Heritage
The legacy of the United States’ Civil Rights history is inescapable on Maryland’s Eastern Shore.
The Harriet Tubman Underground Railroad National Historical Park
The Harriet Tubman Underground Railroad National Historical Park is the most significant place to visit, especially if you are interested in learning more about Harriet Tubman and the Underground Railroad. This important museum and visitor center is an excellent tribute to a national hero and civil rights legend. Bring your kids and start a conversation about racism, slavery, and equality. The exhibits are really well done and educational for kids and adults.
The Harriet Tubman Museum & Education Center
This is another great museum dedicated to Harriet Tubman located in downtown Cambridge. Even if the museum is closed you will want to visit because the outside wall of the museum has the famous mural which shows Harriet Tubman with her hand outstretched, beckoning the viewer to join her on a journey to freedom.
The Harriet Tubman Underground Railroad Byway
This is a self guided auto tour takes you to 30 sites, many of them with outdoor markers or interpretive signs that tell the story of why it is significant. This tour is 125 miles in its entirety and winds through multiple counties on the Eastern Shore.
If the weather is yucky outside there are a few great indoor play places you can visit and let your kids play. Here are our top picks for indoor fun on the Eastern Shore!
- Be With Me Playseum in Easton, MD. This is a great place for imaginative play with different themed play areas and opportunities to do craft or stem projects.
- Cabin Fever Play Centre in Cambridge, MD. They have a designated toddler area, which has small soft climbing toys, a plush carousel ride on, and small slides! It is separated slightly from the bigger kid areas but smaller kiddos are not limited to any one area- they can go to the big play section too.
Visit a State Park
There are quite a few state parks on the Eastern Shore. Here are the ones we recommend the most:
Tuckahoe State Park
This great state park is so much fun for both day trips and weekend trips! There are multiple areas to explore. The Visitor Center has a great aviary, supplies for the disc golf course, and trailheads for over 20 miles of fun trails!
Kids will absolutely love the recycled tire playground on the shores of Tuckahoe Lake. In the Campfire Loop area there are nature trails and another great playground with a fantastic slide!
Pocomoke River State Park
Pocomoke River State Park is such a kid friendly park! I was so impressed! There are two separate areas; The Milburn Landing area and Shad Landing area.
We love the Shad Landing area so much. There are numerous trails, a fantastic nature center, and of course.. the river! In the summer they also have a public pool you can swim in.
Janes Island State Park
One of the things you may have wondered is if Janes Island State Park is worth visiting if you aren’t going to go kayaking or get out on the water… so I checked it out and it totally is!
There is a great little nature center— with a few animals, and great wildlife/bird watching opportunities— including an observation tower!
You can also rent bikes to ride around the non- water trail part of the park. At Tuckahoe Lake you can rent kayaks and canoes seasonally.
Learn to Kayak
Because of all the water trails and calm water areas, the Eastern Shore is a great place to try kayaking. There are a number of places you can actually take beginner kayaking lessons or rent a kayak or canoe for a fairly low price. Here are three ideas:
- Janes Island State Park. This State Park was made for navigating its water trails. If you have kids.. even younger kids— the State Park ranger assured me kayaking and canoeing is not off limits to you. The water in these water trails seems quite gentle and you can rent single or tandem kayaks, canoes, and paddle boards at the marina starting at $35 for a half day. It seems like this would be a great intro!
- Tuckahoe State Park and Martinak State Park. The water trails are gentle in Martinak State Park.
- Chesapeake Bay Environmental Center. If you have nature lovers in your family.. or even aspiring nature lovers.. you HAVE to visit the Chesapeake Bay Environmental Center (CBEC). They are a nature lover’s haven! There are loads of opportunities for hiking, biking, seeing birds, geocaching, and kayaking. You can rent kayaks at CBEC and they even have kid friendly kayak lessons.
Animal lovers will definitely want to check out these experiences on the Eastern Shore!
Assateague National Seashore
There is hardly anything more iconic and completely unforgettable to do in Maryland than go see the wild ponies at Assateague National Seashore.
Apart from trying to find the horses and just enjoying them, there are other fun things to do at Assateague as well. Of course, swimming and hanging out at the beach is a big one. You can actually camp on the beach… which is super cool.
Salisbury Zoo is the best little free zoo in North America! Yep– it’s FREE!
Some of the animals they have on exhibit include the Andean Bear, North American Bison, Tamarin, Wallaby, Alligator, Python, and more! This zoo is located inside Salisbury City Park and is connected to the Ben’s Red Swings playground.
Work Horse Farm Rescue And Exotics
The Work Horse Farm Rescue is such a unique place in Maryland. It’s so worth it to encounter these kind of animals, especially this up close. In the indoor enclosures there is a sloth, porcupines, foxes and other exotic animals. They let you feed the kangaroos. Afterwards you ride a wagon to two different pastures. The farm puts feed on the wagon and the animals come running to eat and greet you. They are always rescuing new animals so new animals are always being added! But they have zebras, wildebeests, water Buffalo, highland cows, camels, ostrich!
Catch a breathtaking sunset
Some of the most beautiful sunsets you can every hope to experience are over the shores of the Chesapeake Bay tributaries and waterways. These are the best places to catch a sunset on the Eastern Shore!
- Crisfield-Wellington Beach
- Deale Island Beach
- The Bayside area of Ocean City (really, a dinner timed for sunset at any of the bayside waterfront restaurants is amazing!)
- Terrapin Nature Park
Visit a Lighthouse
There are 12 lighthouses you can visit in Maryland. Two of them are located on the Eastern Shore! if you want to visit and maybe even tour a lighthouse, check out the Hooper Straight Lighthouse at the Chesapeake Maritime Museum in St. Michael’s, MD. The other lighthouse you can visit is Choptank River Lighthouse in Cambridge, MD.
Whether you enjoy crabs, crab cakes, or something completely non-seafood like a burger, there are some great waterside dining options and award-winning cuisine among the quaint towns of the Eastern Shore. Here are some kid friendly picks we highly recommend!
- Fisherman’s Crab Deck: Just as the name denotes, this is a dockside restaurant that is all about crabs! The menu features fresh fish, shrimp, lobster, clams, and steamed crabs! The kids menu has regular kid friendly options like chicken fingers and burgers. There are ducks for kids to feed as well!
- The Jetty: This is another bay side restaurant option. The Jetty has a sandy beach and sand box complete with beach toys! How cool is that? As for food? Check out their Cream of Crab and Pretzel Combo. Delicious! They have great salads, steamed shrimp and seafood, tacos, burgers, sandwiches, wraps, and seafood entrees. For dessert try the Triple Chocolate Cake or Reeses’ Peanut Butter Pie!
- The Sandbar at Rolph’s Wharf Marina: Located on the Chester river; shallow and calm water. There is a huge bar that serves both alcohol, non alcohol and food (grilled cheese, nuggets, hot dogs, fries, etc). There is shaded seating and outside sand seating with umbrellas and chairs.
Visit a Festival
One of the best ways to explore the Eastern Shore is to attend one of the iconic annual festivals! Ocean City is festival central, but the smaller towns along the way have fantastic festivals too. Here are our top picks!
- Chestertown Tea Party Festival: Every Memorial Day Weekend you can participate in the ultimate American History weekend event! There are opportunities to throw tea overboard, street parties, and a Colonial Parade!
- Berlin Fiddlers Convention: In September every year enjoy bluegrass, gospel, and more!
- Easton Waterfowl Festival: In November you can celebrate everything ducks, decoys, and waterfowl. Kids will absolutely love the Delmarva Dock Dogs and live demonstrations.
- Crisfield National Hard Crab Derby: Every Labor Day weekend. This fun festival features crab races, contests, carnival rides, live entertainment, beauty pageants, a parade, fireworks and more.
Ok, visit Ocean City too!
Clearly, if you are hanging out on the Eastern Shore you will eventually be pulled to the wide open beaches and ocean. Ocean City is always a great idea for family fun! If your Eastern Shore plans include Ocean City, check out these family fun planning resources:
- 10+ Ways to Rock Your Family Vacation at Ocean City
- Ocean City Boardwalk Tips and Things Not to Miss
- Ocean City Restaurants With Playgrounds for Kids!
The Eastern Shore in Maryland is known for pristine beaches, crabs and oysters, lighthouses, gorgeous sunsets, Maryland maritime and civil rights history, the Chesapeake Bay, small historic towns, Ocean City, and the wild horses at the Assateague National Seashore.
Blue crabs, oysters, and rockfish!
Beaches in the Chesapeake Bay area are generally safe to swim in. However, sometimes there is either a high concentration of bacteria or the presence of sea nettles (jellyfish). Check with the local municipality before heading out to make sure it’s safe to swim.
The bottlenose dolphin can be found in the Chesapeake Bay during the summer.
The best small towns to visit on the Eastern Shore are Chestertown, Berlin, Pocomoke City, St. Michael’s, Oxford, and Rock Hall.