Maryland’s Top 6 Summer Road Trip Destinations

Published on July 15, 2020 - Updated on August 20, 2020

A Diverse Landscape Awaits in the State Aptly Nicknamed “America in Miniature.”

Week two of our state-by-state travel highlight reel lands us in Maryland. As we fan out across the country covering all our favorite family-friendly adventures one state at a time, Maryland is the logical next place to launch. 

Known as “Little America,” Maryland, like Virginia (week one’s featured state), is rich in nature of all kinds, from mountains, forests, lakes, rivers, and the great Chesapeake Bay all the way to sandy ocean beaches. It is conveniently located adjacent to the happyly flagship city of DC.

Since we are experiencing the unprecedented life challenges associated with the COVID-19 era, road trips are the wisest strategy for satisfying your family’s summer wanderlust. If you choose to stay somewhere overnight, home rentals with clear sanitization protocols, RV travel, or camping are the safest options for maintaining a physical distance. 

Additionally, as you may expect, weekends can be very busy in state and national parks, so midweek travel is ideal when possible. Whether or not that is an option, we believe with a healthy respect for physical distancing, disinfecting, and strategic mask use, carefully planned adventures are possible.

Outdoor activity and fresh air family fun are always high on our list of priorities. Additionally, variety is also important, suited to a diverse cross-section of landscape and lifestyle preferences, so Maryland is well-suited as our next featured state of the series.

Fun Facts

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Local Maryland blue crab

  • Maryland takes crab consumption very seriously. More blue crabs are produced and consumed in Maryland than any other state.
  • The Baltimore Raven’s are named for Edgar Allen Poe’s poem by the same name - how academic!!
  • Annapolis once served as the capital of the United States.
  • Maryland is at the heart of the lacrosse world, the country's fastest growing sport. The NCAA lacrosse teams of Maryland (including powerhouse Johns Hopkins) have combined for 12 championship wins and more finals appearances than in any other state.

St. Michaels/Tilghman Island

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The "secret" beach in Claiborne

Arriving in this little slice of heaven is like stepping back in time. The warm, welcoming people are just one of many elements that nudge visitors quickly into a relaxed state of mind. 

The neighboring towns have the same quaint appeal. Tilghman Island and Claiborne are sleepy little villages while in St. Michaels there are a variety of shops and restaurants and even more so in the very popular community of Easton, just up the road. They are only around an hour and a half from DC, but they feel worlds away. 

We prefer a happy medium and stay steps from the village of St. Michaels where we can check out shops and restaurants, with easy access to water views. We rent an Airbnb with a meticulous protocol for disinfecting. If a luxury getaway is your preference, The Inn at Perry Cabin is just past town. An additional option is The Wylder Hotel on Tilghman Island, a very lovely property. They both feature alfresco dining, dock access, suite options, and the Wylder is equipped with exterior room entrances.

Riding bikes, fishing, eating, boating, and relaxing are the way of life in this sliver of Maryland. Check out the little “secret” beach in Claiborne, a few minutes from Tilghman Island. Park on the road after the gravel drive before you reach the docks. Walk around 200 yards down the narrow offshoot and find public park access to a lovely little beach. We have found it completely empty as well as busy, but it’s worth checking out for a dip either way as it’s easy to physically distance in the water, as long as the jellyfish aren’t hanging out too.

Patapsco Valley State Park (McKeldin/Cascade Falls)

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McKeldin Rapids

This beautiful park runs along The Patapsco River for 32 miles. There is incredible diversity in the landscape and it is also deeply entrenched in history. The park is spread over more than 16,000 acres so it’s wise to determine your starting point ahead based on your preferred activities, such as hiking, camping, fishing, kayaking, or mountain biking. There are so many trails to explore with all different levels of difficulty - a whopping 73 routes are listed on All Trails where the park is ranked number two out of 906 state parks in Maryland.

Orange Grove is a great place to start, and it is probably the most popular. With hiking, history, architecture, and a lovely waterfall, there is much to see, and it is all manageable on little legs. The parking lot is small, which is both good and bad, as you’ll want to arrive early on the weekends to secure a spot, but if you re lucky enough to get one, you don’t have to worry too much about overcrowding. If the lot is full, give the nearby Glen Artney area a try. 

For a hike that ends in a swimming hole at the base of a waterfall, we love the McKeldin Area of the park. If the parking lot is full, there is a stretch of road where you can park right next to several paths leading you right into the park. Keep in mind, the swimming hole requires traversing a steep set of stairs built into the hill, but if you find it too crowded for your comfort level, you can just wade through the shallow part of the water and continue on your hike. 

Make sure to bring a picnic lunch and plenty of water and snacks because you can easily spend all day in this vast park! If you choose McKeldin, reward your family with a stop at Rita's Italian Ice & Frozen Custard, just seven minutes down Marriottsville Road en route to the highway. If you are camping, the Hollofield Area is popular, and the Hilton area is smaller but seems particularly geared towards children.



The beach at Sandy Point State Park

Only forty miles from DC, this town feels a world away from the city. Kick-off the day at the Annapolis Maritime Museum or wander the beautiful Naval Academy grounds and enjoy views of the Severn River. Grab a picnic lunch and head to Quiet Waters Park, before wandering historic Annapolis and burning some energy at Turner Park where you will find a quiet playground if that appeals to you.

Take a drive over to Sandy Point State Park if time allows. There is a fair amount of room to spread out on the beach and restrictions have loosened up to accommodate safer physical distancing. There is a marina tucked in toward the entrance, hiking trails, and picnic areas with grills. The parking lot does fill up on weekends and gets crowded, so we prefer weekdays. If you decide to wait and make your way over in the late afternoon, you can have a picnic or barbecue and catch the start of a beautiful sunset. 

Alternatively, grab an early dinner at happyly team favorite, Cantler’s Riverside Inn for your Maryland crab fix before heading home or back to a local home rental after a glorious and relaxing day.

Deep Creek Lake


Deep Creek Lake

The largest inland lake in the state of Maryland, Deep Creek has 69 miles of shoreline. While much of that shoreline is private property, Deep Creek Lake State Park has public access and is fairly significant in size. There is boating of all kinds, both motorized and non-motorized. The state park also features great mountain biking, hiking, fishing, and campgrounds with 112 campsites. 

For non-camping families, there are amazing vacation rentals all around the lake. It’s worth noting that homes that face the west side of the lake will enjoy the best sunsets. Stay close to the state park for convenient non-motorized watersports and swimming. If you don’t plan to get out on a boat, there is also excellent fishing from the shore at the park. 

If you are a golfer or are planning to bring your own boat, the northeastern side of the lake is our preference. If adventure activities at Wisp such as the Mountain Coaster appeal to you, find a rental on the northwest side. This will also give you the most convenient access to Swallow Falls State Park and The Youghiogheny River. There you’ll find great hiking as well as three waterfalls including Muddy Creek Falls, the largest freefalling waterfall in Maryland.

Assateague Island (National Park)

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A wild pony on the island

Known for tranquility and untouched beauty, getting away for a quick escape to Assateague Island will compel your whole family to take a deep collective breath. The island provides a true social distancing escape, with miles and miles of beaches to explore.

Development is not permitted on Assateague, so camping is the only option on the island. If you are a camping enthusiast, it is perfect for your family. You can set up on the bay or the ocean sides with daily opportunities to watch wild ponies which have roamed free on the island for centuries, so pack up your RV or rent one. Insider tip, don’t forget the bug spray!!

There are nature trails and hiking, boating, and non-motorized watercraft rentals, and arguably the most beautiful beaches on the Atlantic Coastline. Assateague is a National Wildlife Refuge and is completely undisturbed so it’s wildlife is unreal on the 37 miles of pristine beach.

If you need a true break from the world, this is the place to do it, and if camping is not your thing consider an Airbnb in nearby Berlin or another quaint neighboring town.


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Cunningham Falls

Near the border of Pennsylvania, the name of this town roughly translates to “Gateway to the Mountains.” Appropriately named, it sits at the base of the Catoctin edge of the Blue Ridge Mountains. It is a haven for people who love to explore the outdoors, near both Cunningham Falls State Park and Catoctin Mountain Park. 

Cunningham Falls in The William Houck area of the park is the longest cascading waterfall in Maryland, and there is also a lovely lake in the park with a sandy beach for swimming. You can rent paddle boats and fish in the non-swimming areas of Hunting Creek Lake. There is a nature center and an aviary in the Manor Park area, and while they currently remain closed, the hiking trails and campgrounds have reopened in both spots.

Adjacent to the state parkland at Cunningham Falls, Catoctin Mountain Park is managed by the National Park Service and it is located alongside Camp David. There are great hiking trails there as well, and it is easily accessible from the campgrounds at Cunningham Falls. The Safari Ride Catoctin Wildlife Preserve and Zoo is minutes from both parks, and you can even access the Appalachian Trail nearby.

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Catoctin Mountain Park

Whether you seek ocean beaches, lakes, rivers, waterfalls,islands, thick forests, mountains, farmland or historical landmarks to your heart’s content, Maryland has it all. With so much to visit close to home, people who live in and around the area can experience a new adventure in “Little America” at every opportunity for years to come.

Does your family have a favorite road trip destination? Please reach out to and tell us all about it for future installments of our state to state series! Please tag your summer road trip highlights on Instagram @gethappyly. We love to hear from you!

Be sure to check out State By State Week One: Virginia. We also welcome you to explore our blog for more inspiration such as Build a Summer Bucket List and Camping, Glamping, or RV Travel: What Suits Your Family? or take a few moments to Fill Up Your Tank: Self-Care For Moms to make sure you're ready to give summer all you’ve got!!

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Thoughtfully captured by:
Randi Banks
Randi (Betts) Banks grew up in New York and graduated from Trinity College in Hartford, Connecticut. She moved to Washington, D.C. more than thirteen years ago with her husband, Eaghmon, and they love to explore the area and seek out adventure, now with their two young children along for the ride. Growing up right near the beach, they are happiest when on or near the water, so exploring the rivers, lakes, and streams in the greater DC area is a favorite pastime for their family. In addition to serving as one of the Washington, DC area ambassadors, Randi is also the Editor in Chief and Co-founder of happyly.
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