Aleah and I both grew up in South Central PA and like most from the area, spent at least one week a year on the Eastern Shore of Delaware, Maryland, or Virginia. We lived a brief 25 minutes apart from each other, took the same route to and from, and yet had very different Delmarva experiences with regard to the locations we visited and activities our families chose to do. Right after we started dating, we made a trip together and quickly married our ideas of a weekend best spent by the sea, and we have compiled that list here. To appease my own need to have things in some sort of logical order, let’s go from north to south.
Discover Delaware
Cape Henlopen State Park – This ecologically diverse green space is located just above Rehoboth Beach and offers camping, swimming, picnicking, trails for both biking and hiking, and much more! The 3.3 mile bike loop is a favorite of ours and makes for a very leisurely ride. As far as hiking goes, we love the Walking Dunes Trail which will have your toes in the sand as you stroll over some lightly wooded dunes (2.6mi.) Click here for a park map and take your pick of several other great trails.
Tanger Outlets – Is discount shopping your thing? Tanger Outlets is conveniently located at the entrance to Rehoboth Beach and has all of the large name stores you would expect. We rarely escape Rehoboth without at least cruising through and looking for deals.
Rehoboth Beach – Looking to relax on the beach, do a little seashore shopping, or stroll down a boardwalk? Look no further than the little beach town of Rehoboth! This beach is often viewed as both more family friendly and sophisticated than Ocean City Maryland due to its smaller size, upscale shops, and almost nonexistent boardwalk party scene.
Dewey Beach – If you’re looking to party – Dewey beach is for you. Stop by the Rusty Rudder for some food, a drink, live music, or all three. It’s always a fun time.
Fenwick Island – If you’re looking to do some kayaking or stand-up paddle boarding on a bay with an absurd name, this is your spot. Stop in at Coastal Kayak and book some float time on the Little Assawoman Bay. This place has great prices and a super friendly staff. Make sure to book early/call ahead as this popular boathouse can max out reservations fairly quickly. If you didn’t indulge at the Rusty Rudder, I highly recommend Harpoon Hanna’s for lunch or dinner. Fresh seafood and live music, what more could you ask for?
Pro tip: If you enjoy consuming an alcoholic beverage or two and riding shotgun, crack a beer, or mix up a drink for your ride through DE. This state has no laws against a passenger of a vehicle enjoying an adult beverage. Shout out to Aleah for always being the best chauffeur anyone could ever ask for.
Explore Maryland
Ocean City (OCMD) – Ocean City is large, bustling, and in my opinion, the most fun beach in the region because of its liveliness. With a 2.25 mile boardwalk full of bars, restaurants, carnival games, and an amusement park, this spot on the peninsula is the place to be if you are looking for party vibes at the beach. Visiting OCMD also brings a lot of nostalgia for us along with it, as Aleah and I celebrated *several* “Senior Weeks” here in high school and college. Read our full OCMD Travel Guide here.
Seacrets – Now that we’re in OCMD, it’s time to party, and Seacrets is the perfect place to do just that! Seating IN the bay, live DJ’s all day and night, Rum Runners that will have you questioning whether or not you’re still capable of swimming, and an all around huge party atmosphere are the reasons that Aleah and I have been frequenting Seacrets every trip to the beach since turning 21. If you’re not a drinker or don’t want to get wet, they do have plenty of seating on the shore and away from the fiesta. Their food menu is pretty great too. We swear by the seafood quesadilla and the Jamaican nachos.
If you want a look behind the scenes, Seacrets also offers tours of their distillery – which is a true portal back to prohibition. The tour concludes with a visit to a physician-recommend 1920’s speakeasy where you can sample their products. We found taking shots to be the cherry on top of an awesome experience! 😉
Jolly Roger Amusement Park – Jolly Roger has two locations in OCMD and hosts mini-golf, a water park, go-karts, carnival games, and thrill rides. If you’re tired of the saltwater and sand, the water park part of this whole operation is the most sizable and located within the 30th Street location.
Fish Tales – Fish Tales is a bay side restaurant that is quite possibly our favorite in all of Ocean City. Tables in the sand, adult swings, cold beer, and an all around relaxing vibe is what keeps us coming back for more, not to mention the food is on point. Oh and there is popcorn to snack on while you wait for a table.
Crabs – If you’re craving some Maryland blue crabs, hit either Crab Bag or Hoopers – both offer all-you-can eat steamed crabs, and neither will disappoint.
Wockenfuss Candies – Grab a sweet treat from Wockenfuss Candies, a candy store that’s been around for over 100 years and offers some delicious fudge.
Assateague Island National Seashore – If you want to incorporate some nature into your getaway, hit Assateague Island for some wild horses, hiking, biking, fishing and camping. This 37 mile-long barrier island is home to some pretty interesting wildlife, and provides a great way to get out and explore the edge of the continent. While you’re there, check out the Life of the Dunes trail. On your hike, you’ll cross the historic Baltimore Boulevard, a road intended to connect Baltimore to the Eastern Shore, that was destroyed in a 1962 coastal storm and never repaired. It has a very apocalypse-esque feel to it.
Vacation in Virginia
Chincoteague Island is the state’s only Resort Island and truly the gem of Virginia’s Eastern Shore. The island’s natural beauty and small-town charm is ever-present and truly envelopes you as soon as your cross the causeway. Of the places highlighted here, Chincoteague may be the best for those looking for either a quieter and more relaxing escape into nature or a laidback family getaway. Regardless, there are a few places that you simply cannot leave the island without experiencing…
Chincoteague National Wildlife Refuge is a nature-lover’s paradise. The site is home to 15 miles of trails that weave through maritime forest, dune, and salt marsh habitats, a pristine beach, and the world famous Chincoteague ponies. Whether you want to spend your time here lounging seaside, looking for beach ponies, hiking, biking, or bird watching along the trails, or climbing to the top of the Assateague Lighthouse, you’ll find ample ways to fill your days.
Daisey’s Island Cruises – The best way to see and really learn about the wild ponies is via a guided tour, and recently we had the most incredible experience on one of Daisey’s Island Cruises‘ boat tours. We learned so much from our Captain, Aiden, and spotted not only dozens of wild ponies, but bald eagles, and dolphins too! The best time to see the ponies is in the morning, so it’s best to book a tour for the AM — which will also allow you to beat the heat!
Ropewalk Restaurant – Ropewalk has what we like to affectionately call “yard games” for kids and adults alike. This waterfront restaurant also boasts docks for those who want to visit by boat, palm trees, and tables in the sand. The food and lively, family-friendly atmosphere passes the vibe check, and it’s an all around solid spot for lunch or dinner.
AJ’s On the Creek – For more of an upscale experience, we recommend, AJ’s on the Creek. Aleah swears that she had the best bowl of cream of crab soup she’s ever had here, but we have rave reviews for every one of their made-from-scratch seafood dishes that we’ve tried. AJ’s offer’s outdoor dining on Eel Creek and boasts the title of being the longest-running restaurant on the Island.
Sandy Pony Donuts – This local spot is a Chincoteague institution! The hot and hand-made-to-order donuts at Sandy Pony serves up are both filling and fun to eat and order. Check out their website before you go, so you know exactly what you want because they have 25 different donut flavors to choose from as well as some yummy acai bowls!
Whether you’re indulging in the freshest local seafood, fully embracing your wildlife watching era, lounging on the region’s beautiful beaches or partying along her shores, the Delmarva Peninsula has something for everyone to enjoy – which makes the region perfect for your next summer getaway!
