Chesapeake Road Trip

The Chesapeake Road Trip is an excellent way to explore the Eastern Shore of Maryland. Starting in Elkton, the route takes you 243 km through three towns - Chesapeake City, Chestertown, and Easton - before ending in Tilghman Island. Along the way, you can take in the stunning landscapes of the Chesapeake Bay, explore the many historic sites, and experience the unique culture of the Eastern Shore. The best time of year to drive this route is in the spring or fall, when the weather is mild and the colours of the landscape are at their most vibrant. The road conditions are generally excellent, making the trip easy and safe for any driver. Plus, with a moderate budget, you can make this road trip a truly memorable experience. So grab your keys and hit the road - the Chesapeake Road Trip awaits!

Located in Cecil County, Maryland, United States, Elkton is an ideal starting point for the Chesapeake Road Trip. Elkton is a quaint town with a rich history, offering a variety of landmarks and attractions. Visitors can explore the Elk Landing County Park, the Elkton Railroad Station, the Elkton Armory, and the historic Elkton Town Hall. Popular nearby attractions include the Susquehanna State Park, the Elk Neck State Forest, and the Elk Neck State Park. Those traveling by air can fly into Baltimore-Washington International Airport (BWI) and rent a car from one of the many car rental companies available. From BWI, it is a short drive to Elkton, making it the perfect starting point for the Chesapeake Road Trip. Once in Elkton, visitors can explore the many landmarks, including the historic Elkton Town Hall, the Elk Landing County Park, and the Elkton Armory. Hikers and outdoor enthusiasts can also explore the Susquehanna State Park and the Elk Neck State Forest and Park, which offer a variety of trails and outdoor activities. Elkton is the ideal starting point for the Chesapeake Road Trip, offering a variety of historic landmarks and outdoor activities. With its easy access to BWI and its vast array of attractions, Elkton is the perfect place to begin any road trip.

Embark on a memorable road trip from Elkton to Chesapeake City! This 6mi drive, taking less than an hour, will take you through some of the most picturesque landscapes of Maryland. Start your journey in Elkton, where you can visit the Elk Landing County Park, home to the historic Elk Landing Church. The park is the perfect spot for a picnic or a stroll. As you continue your journey, you will be rewarded with stunning views of the Chesapeake Bay. When you reach Chesapeake City, you can explore the charming streets of the historic district, lined with beautiful 19th century homes. Don't miss the chance to visit the Chesapeake City Museum, which houses a collection of artifacts and documents that tell the story of the city's past. This is one of the stages of a larger tour, and more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route is available in the "Itinerary" of this stage. So start planning your road trip from Elkton to Chesapeake City and enjoy the journey!

Are you looking for an unforgettable road trip experience? Then you should consider a journey from Chesapeake City to Chestertown, which is located only 76 miles away and can be driven in less than three hours. This route takes you through Eastern Neck Island, where you can explore the picturesque scenery and discover historical sites. On your way, make sure to take your time and enjoy the breathtaking views of the Chesapeake Bay. You can also take a stroll along the shoreline, where you can spot some of the local wildlife. As you make your way through Eastern Neck Island, you can visit some of the oldest settlements in the area and explore the rich history of the region. After you reach Chestertown, take some time to explore the charming town and its many attractions. From local shops to unique restaurants, there is something for everyone to enjoy. As you make your way through this beautiful route, be sure to pay attention to the historical sites and the scenic roads that you pass. This is one of the stages of a larger tour, and more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route is available in the “Itinerary” of this stage. So, what are you waiting for? Get ready to embark on an unforgettable road trip adventure!

Are you ready for an amazing road trip from Chestertown to Easton? This stage of your journey will take you 43 mi and less than an hour of driving. You will start your journey in Chestertown and make a stop at the Garfield Center for the Arts at the Prince Theatre. This is a great place to admire the works of local artists and enjoy a variety of art events. Continue your journey to the Pickering Creek Audubon Center, a great place for bird watching and exploring nature. Here you can take a guided tour, attend a workshop or simply enjoy the beautiful scenery. Your next stop is the Talbot County Free Library, the oldest library in Maryland. Here you can find a wide selection of books and other resources. Finally, you will arrive in Easton, where you can visit the Avalon Theatre, a historic theatre with a variety of performances. For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please check the "Itinerary" of this stage. Enjoy your journey!

Start your road trip in Easton, United States and explore the scenic roads of the Eastern Shore of Maryland. In just over an hour, you will be in St. Michaels, a charming colonial town with a rich maritime history. Visit the Chesapeake Bay Maritime Museum and admire the unique boatbuilding culture of the area. Stroll along the waterfront and enjoy the stunning views of the harbor. Then, continue your journey to Tilghman Island, a tranquil fishing village with a rich maritime heritage. Visit the Tilghman Island Museum to learn more about the area’s history and explore the island’s beautiful beaches. As you drive along the scenic roads, take in the stunning views of the Chesapeake Bay and the surrounding countryside. Along the way, you’ll find plenty of places to stop for a bite to eat or a refreshing drink. When you reach Tilghman Island, be sure to take some time to relax and enjoy the peaceful atmosphere. As you explore this beautiful area, you’ll soon see why it’s considered one of the most picturesque places on the Eastern Shore. For more information on attractions, accommodation options, recommended restaurants, and campsites along the route, be sure to check out the “Itinerary” of this stage.

Tilghman Island, located in Maryland, United States, is the perfect place to end the Chesapeake Road Trip. This tiny island is home to a variety of activities and attractions for visitors of all ages. The island is known for its seafood industry, which is a great place to explore and learn about the local culture. Don’t forget to try some of the fresh seafood available in the many restaurants around town. For nature lovers, Tilghman Island offers a variety of outdoor activities such as kayaking, fishing, and bird watching. The island is home to some of the best bird-watching spots in the region, so don’t forget to bring your binoculars. If you’re looking for a more relaxed experience, check out the Tilghman Island Maritime Museum. This museum offers a great opportunity to learn about the history of the area and its many industries. Finally, don’t miss the chance to take a cruise around the island. There are a variety of different tours available, so you can find one that’s perfect for your group. Tilghman Island is the perfect place to end the Chesapeake Road Trip. For visitors flying in, the closest international airport is Baltimore/Washington International Thurgood Marshall Airport (BWI) in Baltimore, Maryland.

Surely, the presented Chesapeake Road Trip gave you multiple inspirations for your future holidays.
The itinerary we’ve suggested can be used as a foundation that you can recreate in its entirety or only partially and that can be enriched with original tourist attractions of your choice.
If car travel is the preferred travel mode for you, there are a number of essential road rules to follow and a number of things to be mindful of to make your trip smooth. The following road rules will surely become useful for all drivers considering renting a car or hiring a camper in Maryland.
It is essential to follow the local road regulations when on a road trip around Maryland. When moving around Maryland in a car, try to avoid spirits at any expense. Holidaymakers ought to remember that the legal alcohol limit for drivers is not very high and equals only 0.5‰. Exceeding the maximum speed limit, which is 40km/h, when driving around the the city streets may result in speeding offence. When travelling in non-build-up areas, you should stick to the maximum allowed speed of 72km/h. Avoid driving faster than the maximum car speed of 129km/h while on motorways. It is best to equip your car with a fire extinguisher and first aid kit and drive with your headlights on at daytime in order to stay safe.
The majority of holidaymakers wonder about the costs of the whole trip. Depending on the budget option of your choice, the amount of money that you have to pay during the whole itinerary can vary. A wide range of budget configurations is showed below.
We estimate that the cheapest offer when it comes to gasoline to cover the planned 5 stages across Maryland can amount to 38 EUR. Economy accommodation options can cost you more or less 154 EUR. The travel expenses related to restaurants and food within this option will cost up to about 144 EUR. If you also aim for the economy car hire offer, you will pay around 90 EUR. Thus, going for vehicle rental will increase the expenses of the road trip from around 336 EUR to about 426 EUR.
Holidayers who are looking for greater comfort and the standard option will pay about 38 EUR for the fuel needed to cover the itinerary. If you are into standard accommodation options, expect that the expenses can amount up to approximately 242 EUR. Travellers can expect that the standard option in terms of food and restaurants will cost roughly 216 EUR. Travellers who want to cover the tour in a standard hire car can expect a cost of roughly 108 EUR. Summing up the standard offer, the estimated cost of the road trip will total more or less 604 EUR for travellers who would like to try car rental and 496 EUR for those who are not interested in renting.
The highest level of comfort of the premium option will live up to the expectations of the most demanding drivers. The whole estimated cost of the tour in this versions of services is 927 EUR with car rental and 496 EUR without a rental vehicle. Travellers who want to cover the tour in a premium hire vehicle can expect a cost of roughly 180 EUR. If you are interested in the premium version of the adventure, the cost of the gasoline needed to cover all stages around Maryland is about 63 EUR. Travellers who will go for top services in all aspects of their itinerary should expect to pay roughly 396 EUR for accommodation options and more or less 288 EUR for restaurants and food.
Our tour is also perfect for camper fans. If you choose this travel mode, the costs will be up to approximately 450 EUR. Camper fans will spend about 63 EUR on fuel allowing to cover all stages of the road trip. Travellers who opt for camper rental should expect to pay more or less 110 EUR for overnight stays and around 144 EUR for expenses connected with food.
All of the details can be easily followed in the section Road Trip Costs.
The period between May and October is great to visit the part of Maryland presented in our adventure idea. If Chesapeake Road Trip has inspired you, you should see other interesting adventures that we offer on our website. We hope that the broad spectrum of ideas will definitely come up to the expectations of the most demanding travellers.