From our condo in Silver Spring, Maryland it takes us about 45 minutes to cross the Bay Bridge (make sure you have an EZ Pass for the toll) and then there are a lot of choices for exploring Maryland’s Eastern Shore. When we first started venturing to the Eastern Shore, I only thought of Assateague and Ocean City, Maryland. Let me assure you, there are a lot of fun places – ice cream shops, cute towns, playgrounds, beaches and art to see! If you prefer staying on Instagram, I have a highlight reel, but I have many more details here and it’s searchable. Some of my hyperlinks below will also take you to my Insta with pics.

Berlin

This is a cute historic town with ice cream, a thrift store (cash only), a coffee shop and some shops. If you pass through on a Sunday, there’s a seasonal market and stores are open too. This is very close to Assateague and Ocean City.

• Island Creamery is located downtown and will let you split a single scoop so you can enjoy two flavors for just over $5. There’s often a line here but it moves fast and you can enjoy seating in the alley next to it.
• Chesapeake Bay Farms is one of the stops on the Maryland Ice Cream Trail; this is directly off US 50 West so it’s an easy stop without adding too much time to your journey
  • You can learn more about it here and the possible prizes!
• The library has toys and is a good stop if you need a clean bathroom.
• The beautifully painted pumpkin scavenger hunt in October was so much fun! It’s free, the town is happening with music and activities for kids. See our reel here.
• About 10 minutes from downtown is Wal-Mart which is a great place to stock up before the beach. We’ve also slept in this parking lot to save money!

Ocean City

This is a destination for many and it’s super fun with the ocean, the bay, a long boardwalk and many other family friendly offerings. We recently found a last minute deal for $92 for the Blue Wave Inn which was like a Motel 6 but with an incredible pool and parking that lasted until 3 pm on the day of check out. It was only 2 blocks from 9th street at the boardwalk. I would stay again.

• No name park is new and a must visit near the skate park and views of the bay.
• Check out CertifiKID* to see if there are any deals for Jolly Rogers Amusement Park (we saw some in June 2024). Many places, like miniature golfing offer deals if you look in hotels at the pamphlets.
• Ocean City is fun in various seasons. We loved visiting in October for the enjoyable weather and the off-season pricing (see what we paid here) at the Francis Scott Key Family Resort which has an indoor pool, putt-putt, free popcorn and a movie room. Insta pics here.

* CertifiKID is very similar to GroupOn. If you’ve never used it, please consider using my referral link as it’s no extra cost to you and I will receive a small credit from CertifiKID. In the DMV, we have found deals for places like DoodleHatch (Columbia), Jolly Yolly (Westfield Montgomery) and HyperKidz.

Bivalve

Cove Road Beach is the only reason we came here which is on a river and very relaxing. It’s about 25 minutes from Salisbury.

Cambridge

Located along the Choptank River, this is a great halfway point to stop and stretch on the way to the Atlantic Ocean. It also makes for a fun day trip from the DMV area (90 minutes from Silver Spring).

• Sailwinds Park has a great playground and is located along the river
• Chick-fil-A is about 1 mile from Sailwinds and has a small play area
• There is a downtown with coffee, ice cream and art! Set your GPS for Black Water Coffee Shop and you’ll be in the heart of it all. IG post here.
• Dorchester County Library is a place to escape the heat but still let your kids stretch. They have kids toys.

Chestertown

This is close to Rock Hall and Betterton Beach. I definitely recommend combining all three for a great day trip away from the DMV. Chestertown is the biggest town and is fun for wandering in and out of shops like the bookstore.

• Betterton Beach is one of those ideal beaches for littles! Check out my IG post. It’s under 2 hours from Silver Spring, MD and we’ve enjoyed this as a day trip.
• Rock Hall – grab a treat at Sweet Cheeks Bakery, grab coffee from Java Rock and look for ospreys at Blue Heron Park.
• Lockbriar Farms for ice cream is part of the Maryland ice cream trail and has delicious fruit flavored ones. The owners had a sweet cat who sat with us and then we took a little tour to see the chickens and flowers blooming.

Easton

Less than 90 minutes from Silver Spring is an Amish Market, indoor play space and great park! It can easily be combined with Cambridge.

• Be with Me Playseum is an indoor playspace with different areas for pretend play, real animals and art. Be sure to check their hours here. This is located on US 50 West. There’s also a location in the Columbia Mall and one in Minneapolis, Minnesota.
• Idlewild Park is an amazing wooden park that’s mostly fenced in, has a tot lot too and bathrooms! There’s also a book box and a really pretty court. IG reel here It’s only a couple of minutes off US 50 East, so it’s another great park on the way to the beach.
• Amish Country Farmers Market – Check their hours and know that it’s closed Sundays. This is a great stop if you just need a quick outting and perhaps some affordable and delicious treats! We love Amish markets and have enjoyed exploring many in the DMV like Annapolis, Laurel and Germantown.
• Chick-fil-A here has a small play area.

Grasonville

The Chesapeake Bay Environmental Center is a great place for getting outdoors, especially if you enjoy walking/hiking or getting out on the water with paddleboards or kayaks. It is exceptionally affordable (like $20/day) and first come first serve. Read more on their site. Grab coffee from Dessert First Dockside Coffee and make sure to check out the marina.

Kent Island

This makes for a great trip and is great when the weather is comfortable for hiking and spending time outdoors.

• Ferry Point Park – Park and check out the Chesapeake Heritage and Visitor Center, then go for a leisurely walk and enjoy the small beach.
• Terrapin Nature Park – This is also a great place to walk and enjoy a small beach.
• Pair with Old Love Point Park or other fun from Stevensville or Grasonville.

Oxford

I could come here just for the uniqueness of the ice cream! There is a small town along Main Street, a playground with shade near the water and a small beach.

• Scottish Highland Creamery is so cute and right on the water!
• Main Street has a little museum, a cute store of 30+ local vendors called the Treasure Chest, a market, Mystery Lovers Bookstore and my personal favorite was my iced lavender latte at Oxford Social Cafe. There’s a playground on the water and a little beach too.

Salisbury

This is the great stop to break up the drive to or from the ocean or to enjoy as its own trip.

• Free (donation based) Salisbury Zoo with Ben’s Red Swings Community Playground next to it
  • The zoo is typically open 9 am – 4:30 pm, https://salisburyzoo.org/.
  • Lots of great animals like wallabies, Canadian lynx, eagles, prairie dogs, bison, etc.
  • Recommend parking on the side closer to the playground
• Henry S. Parker Athletic Complex, which is an accessible playground and has a trail near it
• Try Rise Up Coffee and nearby ice cream at Two Scoops Ice Cream and Waffles in downtown
• Oakley’s Farm Market is right off US 50 West near Salisbury in Hebron. It has a playground! They have pick your own and ice cream too! We loved stopping here in October for pumpkins.

Stevensville

Will travel for ice cream should be our middle names. You can have a great day between the beach, ice cream and playground all within a short distance of one another.

• Historic downtown Stevensville is small, but worth visiting for the Tasty Toucan which has a very kid friendly outdoor space. Check out my IG post.
• Matapeake Beach is a small beach nearby. Parking is limited so get there early or come later in the day.
• Old Love Point Playground

St. Michael’s

There’s a Saturday morning market and the library has toys if you’re visiting with a young child. It’s a fun town by the water. Grab coffee at Blue Crab and check out my IG post here.

So much to do on the Eastern Shore

If you have time and like birding, bring your camera and check out Blackwater National Wildlife Refuge and the nearby Harriet Tubman Underground Railroad Visitor Center. And why not venture all the way to Delaware! You’re almost there anyways. Here’s our day in Rehoboth. I also have a beach highlight on Instagram that some of the beaches we’ve been to within a reasonable drive of the DMV.

Let me know in the comments what you love about the Eastern Shore or somewhere we should visit on a future trip!