Best Day Trips in Maryland
Ready to unplug from the daily routine and take a day trip from the city? Well, you are in the right place! Whether you're into history, nature, or beaches, Maryland is a wonderful place for day trips. The best thing is that Maryland offers a variety of experiences just a short drive from one another.
You can stroll through historic towns, go hiking, enjoy waterfront spots kids, or romantic dining by the bay. Here are the trips I recommend from my recent four week road trip through Maryland, and I think you’ll enjoy them too.
1. Chesapeake Beach
I thought that Chesapeake Beach was one of the best day trips in Maryland when I moved to the East Coast. Why? We loved that it's close to both DC and Annapolis and offers an incredibly relaxing setting.
When I first visited Chesapeake Beach, I couldn’t believe how close it was to Washington, D.C., and yet it felt like a world away. Just about 40 minutes from the city, this coastal town quickly became one of my favorite Maryland escapes. We stayed at 4-star Chesapeake Bay Beach Club & Spa for two days. I kicked off my weekend with a 60-minute classical massage which was 100% worth it!
You should start along the waterfront boardwalk to stretch your legs after the drive. The views of the Chesapeake Bay are so relaxing coming from the cement jungle of a city. The breeze, the salty air, the sound of seagulls made me want to stay all day.
If you are feeling active, hike along the Chesapeake Beach Railway Trail, which winds through marshes and wetlands. It's so peaceful there!
I always enjoy a good seafood meal on my weekend trip, and Chesapeake Beach delivers. We grabbed a table at Baia Coastal Italian Kitchen & Wine Bar which had incredible ocean views and fresh seafood.
For a bit of fun, we also stopped by the Chesapeake Beach Water Park. You should try it in the summer, your kids will thank you.
We ended the day watching the sunset over the Bay which was my personal highlight. The colors reflected on the water were pink like in this photo.
- Location: Map & Directions
Whenever people ask me about the best quick getaway near D.C., Chesapeake Beach is the first that pops into my head because everyone relaxes by the water!
2. Bethesda - 30 minutes from D.C.
I think of Bethesda is the second best option for a fun day trip in Maryland. Why? First off is't just 25 minutes outside Washington, D.C. so you can drive there for 2 hours and hit a reset button on your stress in no time. It’s so close to the capital but it totally feels like its own unique destination that completely won me over.
Stretch your legs and let kids run along the Capital Crescent Trail. The shaded paths let you walk or bike on it at your own pace.
Downtown Bethesda has cool cafes, boutiques, and restaurants that gave the area a modern vibe. It’s the kind of spot where you can sip coffee in the morning and enjoy cocktails in the evening without leaving the same block.
Bethesda Row with its shops, galleries, and eateries, was the heartbeat of the town. I could easily spend hours at this underrated urban gem hidden in the suburbs.
Food is a big part of a satisfying day trip Bethesda didn’t disappoint. A great spot for soups and salads along Bethesda Row is maman. We picked up snacks at French Press and ate them later.
- Location: Map & Directions
By the end of the day, I think you'll agree that Bethesda is more than just a suburb near D.C. It's it's own destination filled with energy, culture, and small-town charm.
My personal highlight was watching my son play at KID Museum. There's coding, robotics, woodworking, textiles...you can let your kids play here all day!
3. Germantown
When I made a day trip to Germantown, I was struck by how it felt both so laid-back and slower-paced which was just right for a day trip from the city. Just 30 miles northwest of Washington, D.C., it’s one of those underrated Maryland towns that makes you want to come back for another visit.
We drove north from Bethesda in about twenty minutes, through patches of woodland before arriving in Germantown.
We started at Seneca Creek State Park, my favorite stop of the day. I loved wandering down the wooded trails and enjoying the peaceful views around Clopper Lake. It felt like such a hidden escape where I could just breathe and recharge.
Downtown Germantown has a totally different vibe. I enjoyed walking around the Town Center with its shops, cafés, and restaurants. It’s not huge, but it has a cool community.
If it's cold out, catch a show at the BlackRock Center for the Arts. It's an easy way to add a cultural experience to your outing.
We liked how affordable Germantown was compared to bigger Maryland cities. We found plenty of casual dining options and cozy coffee shops where I could relax without breaking the budget.
- Location: Map & Directions
My favorite highlight was the fall pumpkin festival at Butler's Orchard, second favorite here is apple picking, also in the fall!
4. Sandy Point State Park
If you are in the mood for a day trip to the beach, head to Sandy Point State Park just outside Annapolis and right by the Chesapeake Bay Bridge. Just a 15-minute car ride from the city brings you to the sandy shore and ocean. It's easy and cheap so don't skip this fun spot!
We headed straight for the sandy beach, and I loved how relaxed the atmosphere was. Families were swimming, people were fishing off the pier.
You can enjoy being active on the water with swimming, launch a kayak, followed by a picnic under the shady trees.
There are cool trails through wetlands and wooded areas if you want to get active. I spotted herons and other birds during our walk.
Keep in mind that there's a $5 per person entrance fee. Still, it's an affordable way t to spend a day without having to drive far.
- Location: Map & Directions
My favorite part of the day was sunset over the bay!
5. Salisbury
Just about 30 minutes from Ocean City, Salisbury, Maryland makes for a cool day trip stop inland. It offers culture, history, and outdoor fun so there's plenty for you to do. I definitely thought that Salisbury is an underrated inland town that should be on the map! Best of all, if you are into sunsets over the water, you can catch one here too...over the river!
The best place to start exploring Salisbury is definitely downtown! The streets have a cool artsy vibe that's easy to enjoy.
We took some time to explore Salisbury University’s campus which has lovely landscaping, sculptures, and community energy from the students and faculty.
My son enjoyed the Salisbury Zoo for two hours, which was free (including free parking!). If you have kids, there's no reason to skip it! It’s small but thoughtfully designed. You can see animals up close in a family-friendly setting, plus there's a playground for little kids.
If you are in the mood for fresh Maryland seafood, have lunch at Mogan's Oyster House. For some unique flavors, I like KOJI, serving unique Japanese and Korean dishes.
- Location: Map & Directions
My favorite highlight was watching the sunset over the rived at Brew River right from the river dock.
6. Oregon Ridge Park and Lodge
Another inland favorite of mine, Oregon Ridge Park in Cockeysville, just 30 minutes north of Baltimore is a super cool place if you like being surrounded by nature. It’s one of the best spots for anyone who wants a quick outdoor getaway without going too far (or spending too much).
We started with a hike on the trails in the morning. It was truly peaceful walking through dense woods and open meadows. The bird calls gave the whole place a calm vibe that made me easily forget I was so close to Baltimore.
There is even a hidden lake in this park! We sat by the water and had a small snack before continuing.
Oregon Ridge is also home to a nature center, which I thought was awesome. It’s full of exhibits and activities for kids like maple sugaring weekends and music events. These events make it great for family outings. I enjoyed learning more about the local plants and wildlife too.
- Location: Map & Directions
By the end of the day, I thought how lucky Baltimore residents are to have such an an underrated Maryland gem right on their doorstep!
7. Assateague Island
Assateague Island is such a cool, wild place! It's definitely one of my favorite day trips in Maryland but I recommend getting an early start so that you can enjoy the island for several hours before heading back home. Catch a ferry from Ocean City for scenery from the water (or you can drive there-it's about 20 minutes if it's low traffic).
It's all about nature here, so it's best to be prepared with sunscreen, comfortable clothing and shoes, hats. Walk along the sandy shoreline and look for wild pinies along the way.
The trails through dunes and marshes are super fun to explore. Each turn gets you to something new, like herons wading in the water looking for food, crabs on the sand, and wildflowers especially in the spring.
Camping on the island is an awesome experience too and on my bucket list for next time. I can't wait to see the night sky above and then fall asleep with the sound of waves.
- Location: Map & Directions
Assateague Island is one of the best day trips in Maryland if you love beaches and pristine nature.
8. Ocean City, MD
No post about the best day trips in Maryland could be complete without Ocean City, Maryland! When I think about Ocean City, I remember long stretches of sandy beach and a lively boardwalk that couldn't have been better for family summer fun. We drove 2 hours 45 minutes from Washington, D.C. (it's about the same from Baltimore) so we decided to turn the day trip into a weekend getaway and checked into 4-star Hilton Ocean City Oceanfront Suites. It was already low season in October so our suite for two days was surprisingly affordable and right on the ocean. I ended up recommending it to friends looking for an anniversary vacation.
We started each morning with a walk along the famous three-mile boardwalk. It was my favorite part of the trip and completely free! The ocean views were lovely. For kids there are arcades, shops for adults, and food stands when you get hungry!
I couldn’t resist grabbing Thrasher’s Fries, and later we cooled off with some saltwater taffy. Yes, it's touristy but it's part of the vibe here that you are pulled into!
During the afternoon, we relaxed on the beach itself. It was too cold to swim in October, so we watched the waves roll in. There are also boat tours if you are looking for more to do.
- Location: Map & Directions
My personal highlight was riding on the Ferris wheel which luckily was still operating in October.
9. North Beach
Another cool beach spot that's underrated compared to Ocean City but just as cool is North Beach, Maryland. Some people might prefer it because it's just an hour from Washington, D.C. which means less driving and more time relaxing with a view of the water. That's my this little town on the Chesapeake Bay is one of my favorite day trips in Maryland and East Coast.
We drove south from Annapolis as part of a longer road trip for about forty minutes. The road passed through small towns and farmland before opening to the shoreline at North Beach.
Again, we started with a walk along the waterfront boardwalk. Just like in the picture, the boardwalk is full of pink and red flowers. It's so lovely with ocean on one side and flowers on the other.
The beach here is smaller but welcoming.
A cool spot for lunch is the bakist. It's tiny but it makes really good pancakes.
- Location: Map & Directions
We timed our visit to the North Beach Pier to catch the sunset on the Chesapeake Bay, definitely my personal highlight!
10. St. Michaels
In December, St. Michaels was full of holiday cheer. This quaint Chesapeake Bay harbor town was a perfect holiday day trip in Maryland! I could see why it's often called the “Nantucket of the Chesapeake”...it really was a postcard-perfect holiday village!
You can catch The Christmas in St. Michaels Festival, a tradition that spans decades! They offer horse-drawn carriage rides, boat parades and choirs.
We stayed at 3-star St. Michaels Harbour Inn, Marina & Spa for two days.
It gave us enough time to go to the Chesapeake Bay Maritime Museum and the Classic Motor Museum, explore the 1879 Hooper Strait Lighthouse, and enjoy local food. Outdoor activities such as boating, sailing, kayaking, and the Patriot Cruises are also popular in the summer, as is browsing the shops and the local Farmers Market.
My favorite highlight was deciding which amazing restaurant to try for our evening meal. You can go for creamy crab bisque and warm oyster stew at The Crab Claw, followed by a nightcap at a fireside tavern glowing with Christmas lights and laughter. Our weekend felt timeless, touched by the gentle rhythm of coastal winter life.
Conclusion
After exploring so many of these destinations, I’ve come to realize that Maryland is filled with an exciting mix of coastal escapes, small-town charm, and outdoor adventures.
What stood out to me most is how joyful these trips can be, no matter what kind of traveler you are. Families, couples, or even solo explorers will find something spectacular—whether it’s history, food, nature, or simply a quiet moment by the bay.
For me, the magic of Maryland day trips lies in their variety and simplicity. You don’t have to go far to feel like you’ve escaped somewhere special. Each destination leaves you with memories that are worth far more than the miles it takes to get there.
If you’re looking for the absolute best way to enjoy Maryland, start with a day trip—you’ll quickly see just how many gems are waiting right in your backyard.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
5. If you are planning to visit more than three national parks in the next 12 months, buy the America the Beautiful Pass.
