2 Day Getaway to MD/VA Eastern Shore - Retire With Me Cindy Marie

Two Day Itinerary for Virginia/Maryland Eastern Shore Road Trip

For a quick two-day getaway, we decided to check out Virginia’s eastern shore since we had never been there. It did not disappoint. From southern Maryland, we travelled south through Hampton Roads VA and around to go through the Chesapeake Bay Bridge Tunnel to the eastern shore. (It was ~3.5 hours from La Plata MD.) If you had not been over/through the tunnel, it is approximately 18 miles of alternating bridges and tunnels over the Chesapeake Bay. The scenery is gorgeous. We then travelled north towards the Maryland side of the eastern shore hitting the sights along the way.

This trip starts and ends in southern Maryland, but you can adjust based on where you start.

Links are provided to each of the sights listed.

First stop: CAPE CHARLES VA – 20 minutes – 15 miles from Chesapeake Bay Bridge Tunnel

Cape Charles, Virginia is a small, historic bayside town on the southern tip of Virginia’s Eastern Shore, known for its relaxed atmosphere, scenic beaches, and charming downtown. It blends Victorian-era history, Chesapeake Bay beauty, and a laid‑back coastal lifestyle that draws both weekend travelers and long‑term residents.

Sights to See:

Cape Charles Beach – Situated along Bay Avenue, it a very laid back cove of a beach on the Chesapeake. There are very little waves and it is shallow for a long way out. It is perfect for families with small children to play in sand and in the water and very relaxing for adults as well. Great photo op at the Cape Charles LOVE sign.
Walk shops along Mason Avenue
- Gull Hummock Gourmet Market– fine wines, cheeses, craft beers, locally made chocolates, and gourmet and gluten-free foods
- Drizzles– store for chefs, home cooks, and foodies. They’ve got grilling salts, peppercorns, herbal raw honey, BBQ sauces, mustards, stuffed olives, organic spices, gourmet olive oils and balsamic vinegar
- Beach Market– one-stop shop for fresh seafood, hand-cut meats, and gourmet goods direct from the local fishing, farming, and wine-making industries. Popular gift options include their wines and gourmet cheeses
- Brown Dog Ice Cream – a small‑batch, handmade ice cream shop known for creative flavors, local ingredients, and a classic small‑town coastal vibe.
- Other clothing and gifts shops and candy and specialty stores
- Photo op at Cape Charles Mural.

Restaurants:

The Shanty Restaurant – Excellent casual seafood restaurant right in the Cape Charles Harbor. Indoor and outdoor seating. Great views.

Cape Charles Brewing Company – located on Stone Road, the main road into Cape Charles. A family friendly brew-pub with plenty of indoor and outdoor seating and entertainment on the weekends. Beer, burgers, and seafood sandwiches.

AJs Bar & Grill – Nice little bar & grill right in the heart of Bay Street downtown. Reasonably priced American fare.

2nd stop: Chincoteague Island VA – 1 hr 28 min – 73 miles from Cape Charles

Chincoteague Island is a charming resort island on Virginia’s Eastern Shore, famous for its wild ponies, natural beauty and outdoor adventures.

Sights to See:

Robert Reed Waterfront Park – small waterfront park with pier fishing, boatslips, covered pavilion and picnic tables. Home of the Misty of Chincoteague Statue and HUGE ornamental Adirondack chairs great for photo ops.

Chincoteague National Wildlife Refuge – a protected coastal refuge on the southern end of Assateague Island in eastern Virginia. It is famous for its population of wild Chincoteague ponies, which graze in the marshes and are managed by the local volunteer fire company. Visitors also come to see bald eagles, herons, ospreys, snow geese, and many other bird species throughout the year.
- Many nature trails for hiking and biking
- Drive the Wildlife Loop in search of ponies and other wild life – open to vehicles every day 3pm to dusk. We saw about seven ponies in the distance there and more on Beach Road heading out to the public beach area.
- Nice large public beach area – amazing views of Atlantic Ocean on one side and Chincoteague Bay on the other side.
- Assateague Lighthouse – Historic lighthouse built in the 1860s. Open to climb to the top on weekends from April to September, but the grounds are accessible every day year round

Drive around the town:
- Check out the key locations associated with the annual pony swim—Veterans Memorial Park, where spectators view the ponies swimming across from Chincoteague National Wildlife refuge, and parade route from Pony Swim Lane to the Chincoteague Carnival Grounds on Main Street.
- Check out shops along Main Street and Maddox Boulevard
  - The Brant Gift Shop – large shop with wide variety of souvenirs and gifts. Worth a stop.
  - Hansen’s Craftory – small shop selling homemade candles, soaps, essential oils and other gifts.
  - Whiteraven’s Nest – gourmet farm market grocery store with canned locally canned fruits, veggies, pickles, dressings, sauces and spices as well as meats and fresh vegetable.
  - Sunsations Outlet (6318 Maddox Road) – Just like the Sunsations you find in Ocean City but an outlet. Go here if you are just looking for a Chincoteague t-shirt or sweatshirt or other souvenirs—prices of the shirts and clothing in other shops are outrageous.

Restaurants:

Backfin Island Grill – Very good restaurant with bar. Serves tacos, wings, sandwiches, poke bowls, salads and seafood baskets. It also has amazing brick oven pizzas!

Ropewalk Chincoteague – Owned by the same people that own the Ocean City Chincoteague. It’s a family friendly seafood restaurant with gorgeous water views of the Chincoteague Bay. There is indoor seating as well as outdoor seating in the sand, and a children’s play area too.

Hotel:

Fairfield Inn or Spark by Hilton (~$150-$200)

3rd stop: Assateague State Park MD – 1 hr – 51 miles from Chincoteague, VA

For another chance to see ponies, we stopped by Assateague State Park on the Maryland side of Assateague Island. It is located on Assateague Island between the Atlantic Ocean and Sinepuxent Bay. The park offers 2 miles of beaches for swimming, sun bathing, surfing and fishing, in addition to canoeing and kayaking on the bay side. There are also designated areas for camping. When we were there, we saw more ponies in Assateague State Park than in Chincoteague. They were right on and along the roads and parking lots and fields close to the roads.

4th stop: Berlin MD – 15 min – 10 miles from Assateague State Park

Berlin is a historic small town with Victorian architecture and very walkable Main Street with cute little shops, galleries, antique stores and restaurants. We walked up and down Main Street and perused the shops for a couple of hours.

Recommended Restaurant: Roadie Joe’s Bar & Grill – wide variety of appetizers, subs, sandwiches, salads and rice bowls.

Interesting Notes on the Ponies

Assateague Island is split by both Maryland and Virginia.
The Chincoteague National Wildlife Refuge is on the Virginia side and the Assateague State Park is on the Maryland side.
There are two distinct herds of ponies separated by a fence on the state line.
The ponies are believed to descend from Spanish horses shipwrecked or brought by early settlers in the 16th or 17th centuries.
Maryland ponies
- There are less than 100 ponies on Assateague State Park.
- They are 100% feral with very minimal human intervention, except for contraceptive measures to prevent overpopulation.
- They are monitored from a distance by the National Park Service.
Virginia ponies
- There are approximately 150 ponies on the Chincoteague National Wildlife Refuge.
- They are owned and managed by the Chincoteague Fire Department.
- They are monitored and given health checks and vaccinations throughout the year.
- There are generally around 60 new foals born each spring.
- They are slightly taller and more stout than the Maryland ponies.
The famous Pony Swim includes only the Chincoteague ponies. In order to manage the population of the herd, at the end of every July, they are rounded up and some are selected to swim from the refuge on Assateague onto Chincoteague Island to be auctioned to buyers.
Thousands come each year to see the swim and then the ponies parade down Main Street to the fairgrounds, where the auction is held and there is a huge celebration and carnival.
Most people don’t know that there are also spring and fall round-ups of the ponies, where they are counted and vet checked. Although they do not do the swim over to Chincoteague Island, there is an opportunity for the public to view the round and see the ponies more close-up without the massive crowds of the July Pony Swim.
NOTE: On our trip in May, we saw more ponies on Assateague than Chincoteague, and they were very close to the road and even on the parking lots. The Chincoteague ponies were further away from the roads and trails, grazing out in the marshes and fields.