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Weekend Getaways Maryland: Escape the Mundane and Explore the Charm of the Old Line State

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by Trip.com

Introduction

Tired of the monotony of everyday life and in dire need of a break? If you're based in the East Coast, Maryland is an ideal destination for a weekend getaway. Whether you're a history buff, a nature lover, or a foodie, Maryland has something to offer everyone.
weekend getaways maryland - Fort McHenry Tunnel

Fort McHenry Tunnel / Source: Trip.com

From the bustling city of Baltimore to the serene beaches of the Eastern Shore, there's no shortage of options for a quick escape. In this article, we'll explore the top weekend getaways Maryland has to offer, so you can plan your next adventure with ease.
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1. Chesapeake Bay: A Waterfront Haven

Chesapeake Bay Bridge-Tunnel

Chesapeake Bay Bridge-Tunnel / Source: Trip.com

Are you in need of a relaxing weekend getaway surrounded by breathtaking water views? Chesapeake Bay is the perfect waterfront haven to satisfy your cravings for tranquility and rejuvenation. This East Coast gem offers a wide range of water activities, sandy beaches, and delicious seafood options for every palate.

👉 So, pack your bags, grab your sunscreen, and get ready for an unforgettable Chesapeake Bay adventure.

Sunset Dolphin Kayak Tours

Accommodations in Chesapeake Bay

Chesapeake Bay offers a range of lodging options to fit any budget and preference. For a luxurious stay, check out the waterfront resorts and boutique hotels that dot the shoreline. For a more rustic experience, try camping at one of the many state parks in the area.

How to get to Chesapeake Bay?

Now, let's talk about how to get there. The easiest way to reach Chesapeake Bay is by car. Just hop on I-97 and follow the signs to the bay. Alternatively, you can take a scenic drive along the Eastern Shore and soak up the beautiful views along the way.
If you prefer public transportation, the Maryland Transit Administration offers a bus service from Baltimore to Annapolis, which is just a short drive from Chesapeake Bay. From there, you can take a taxi or rideshare service to your accommodations.
Flights to Chesapeake

2. Baltimore: A City of Charm and History

weekend getaways maryland - Inner Harbor

Inner Harbor / Source: Trip.com

Baltimore, a city that's full of character and history, offers visitors a taste of Maryland's charm. Whether you're a foodie looking for a unique culinary experience or a history buff eager to explore the city's past, Baltimore has something to offer.

👉 With its charming neighborhoods, iconic landmarks, and diverse art and culture scene, Baltimore is a weekend getaway that won't disappoint.

Baltimore Inner Harbor Sunset Sail

Accommodations in Baltimore

👉 Looking for a fun weekend getaway in Baltimore? Let's start by finding the perfect accommodations.

Baltimore has plenty of lodging options to fit any budget and preference. From chic boutique hotels to cozy bed and breakfasts, you're sure to find a place that suits your style. For those on a budget, there are also plenty of affordable chain hotels and motels in the area.

How to get to Baltimore?

Now, let's talk about how to get to Baltimore. The city is easily accessible by car, as it's located at the crossroads of several major highways, including I-95 and I-83. If you prefer public transportation, Baltimore also has a robust public transit system, including light rail, metro subway, and bus routes that connect to surrounding areas.

👉 If you're flying into the city, Baltimore/Washington International Thurgood Marshall Airport is located just 10 miles south of downtown Baltimore. From there, you can take a shuttle, taxi, or rideshare service to your accommodations.

Flights to Baltimore

3. Annapolis: A Colonial Capital

Annapolis city view

Annapolis city view / Source: Trip.com

Annapolis, the capital of Maryland, is a charming town that seamlessly blends old-world charm with modern conveniences. This colonial capital boasts a rich history, vibrant art scene, and fresh seafood, making it the perfect weekend getaway destination.

👉 Whether you want to stroll through the historic streets, sail on the Chesapeake Bay, or indulge in the local cuisine, Annapolis offers plenty of activities to make your weekend memorable.

Annapolis Scavenger Hunt

Accommodations in Annapolis

👉 Looking to explore the charming city of Annapolis for your next weekend getaway? Let's start by finding the perfect accommodations.

Annapolis offers a range of lodging options to fit any style and budget. From luxurious waterfront resorts to quaint bed and breakfasts, you'll find a place that feels like home. For those on a budget, there are also plenty of affordable hotels and motels in the area.

How to get to Annapolis?

Now, let's talk about how to get to Annapolis. If you're traveling by car, Annapolis is located just off of Route 50 and is easily accessible from both Washington D.C. and Baltimore. If you prefer public transportation, you can take the MARC train from Union Station in Washington D.C. or the Baltimore Penn Station to the Annapolis Junction Station. From there, you can take a taxi or rideshare service to your accommodations.
If you're flying into the area, both Baltimore/Washington International Thurgood Marshall Airport and Reagan National Airport are within easy driving distance of Annapolis. From there, you can rent a car or take a shuttle, taxi, or rideshare service to your accommodations.
Flights to Annapolis

4. Assateague Island: A Wildlife Getaway

weekend getaways maryland - Assateague Island

Assateague Island / Source: Joseph Holihan @ unsplash

Looking to get up close and personal with Maryland's wildlife? Look no further than Assateague Island. This barrier island, situated off the coast of Maryland, offers visitors a chance to witness wild horses, dolphins, and other marine life in their natural habitat. With its sandy beaches, hiking trails, and diverse wildlife, Assateague Island is a perfect weekend getaway for nature lovers.

Accommodations in Assateague Island

👉 Ready for a weekend of relaxation and adventure on Assateague Island? Let's start by finding the perfect accommodations.

Assateague Island offers a range of lodging options to fit any style and budget. From campsites to cabins to beachfront hotels, you'll find a place to suit your needs. For a truly unique experience, try camping on the island and falling asleep to the sound of the waves.

How to get to Assateague?

Assateague Island

Assateague Island / Source: Trip.com

Now, let's talk about how to get to Assateague. The island is located on the coast of Maryland and Virginia and is easily accessible by car. Just take Route 50 to the coastal town of Berlin, Maryland, and then head south on Route 611 to reach the island. If you prefer public transportation, there is a shuttle service that runs from the town of Berlin to the island during the summer months.
If you're flying into the area, the closest airports are Salisbury-Ocean City Wicomico Regional Airport in Maryland and Norfolk International Airport in Virginia. From there, you can rent a car or take a shuttle, taxi, or rideshare service to reach the island.

5. Deep Creek Lake: A Year-Round Adventure

Deep Creek Lake

Deep Creek Lake / Source: Justine Kirk @ unsplash

Deep Creek Lake is a four-season playground that offers a wide range of activities all year round. Whether you're looking to ski in the winter, kayak in the summer, or hike in the fall, Deep Creek Lake has something for everyone.

👉 This stunning mountain lake also offers visitors a chance to stargaze at night, making it a perfect destination for those looking to escape the hustle and bustle of city life.

Accommodations at Deep Creek Lake

👉 Looking to escape to the natural beauty of Deep Creek Lake for your weekend getaway? Let's start by finding the perfect accommodations.

Deep Creek Lake offers a variety of lodging options to fit any taste and budget. From cozy cabins and vacation homes to luxury resorts and hotels, you'll find a place to suit your needs. And with stunning lakefront views and access to outdoor activities like hiking, boating, and skiing, you'll be sure to have a memorable experience.

How to get Deep Creek Lake?

  • If you're driving, take Interstate 68 to Exit 14A and follow the signs to Deep Creek Lake. You'll pass through charming towns like Accident and Oakland before reaching the lake. If you prefer public transportation, there are bus services that run from major cities like Baltimore and Washington D.C. to the nearby town of Oakland. From there, you can rent a car or take a taxi or rideshare service to reach your accommodations.
  • If you're flying into the area, the closest airport is Pittsburgh International Airport, which is about two hours away by car. You can also fly into Baltimore/Washington International Thurgood Marshall Airport or Dulles International Airport, which are both about three hours away by car.

6. Ocean City: A Beach Lover's Paradise

Ocean City Beach

Ocean City Beach / Source: Trip.com

If you're a beach lover looking for the perfect weekend getaway, Ocean City is your dream destination. With its sandy beaches, iconic boardwalk, and exciting amusement park rides, Ocean City is the ultimate beach lover's paradise. This charming town also boasts fresh seafood, cozy beachfront hotels, and a lively nightlife scene, making it a must-visit destination.
Tandem Kayak Rental

Accommodations in Ocean City

Ocean City offers a variety of lodging options to fit any style and budget. From cozy bed and breakfasts to beachfront hotels and resorts, you'll find a place to suit your needs. And with miles of pristine beaches, a bustling boardwalk, and plenty of outdoor activities, you'll have plenty to keep you entertained.

How to get to Ocean City?

  • If you're driving, just take Route 50 all the way to the coast and follow the signs to Ocean City. If you prefer public transportation, there are bus services that run from major cities like Baltimore and Washington D.C. to the nearby town of Salisbury. From there, you can take a taxi or rideshare service to reach your accommodations.
  • If you're flying into the area, the closest airport is Salisbury-Ocean City Wicomico Regional Airport, which is about 30 minutes away by car. You can also fly into Baltimore/Washington International Thurgood Marshall Airport or Ronald Reagan Washington National Airport, which are both about two hours away by car.

7. St. Michaels: A Quaint Escape

St. Michaels Sea View

St. Michaels Sea View / Source: Trip.com

If you're looking for a quiet, quaint escape from the hustle and bustle of everyday life, St. Michaels is the perfect weekend getaway destination. This charming town on Maryland's Eastern Shore offers visitors a chance to wander through picturesque streets, indulge in fresh seafood, and enjoy a Chesapeake Bay wine tour. Whether you're looking for a romantic getaway or a peaceful retreat, St. Michaels is the perfect destination.

Accommodations in St. Michaels

St. Michaels offers a range of accommodations, from cozy bed and breakfasts to luxurious waterfront resorts. With its picturesque harbor, quaint shops, and renowned seafood restaurants, it's the perfect place to relax and unwind.

St. Michaels Inn

1228 South Talbot Street | 2.29km from downtown
No breakfast

Swimming pool

Wi-Fi

Parking

Check Availability

How to get to St. Michaels?

  • If you're driving, just take Route 50 to Easton and follow the signs to St. Michaels. If you prefer public transportation, there are bus services that run from major cities like Baltimore and Washington D.C. to Easton. From there, you can take a taxi or rideshare service to reach your accommodations.
  • If you're flying into the area, the closest airport is Baltimore/Washington International Thurgood Marshall Airport, which is about 90 minutes away by car. You can also fly into Ronald Reagan Washington National Airport, which is about two hours away by car.

8. Frederick: A Cultural Hub

Historic Downtown Frederick

Historic Downtown Frederick / Source: Trip.com

Frederick, a cultural hub in Maryland, offers visitors a chance to indulge in history, art, and culinary delights. This charming town boasts a rich Civil War history, a vibrant arts scene, and craft beer and wine galore. Whether you're interested in visiting museums, taking a ghost tour, or exploring the historic district, Frederick has something to offer everyone.
Walking Tour

Accommodations in Frederick

Frederick offers a range of accommodations, from cozy bed and breakfasts to modern hotels and resorts. With its charming downtown area, beautiful parks, and rich history, there's something for everyone in Frederick.

How to get to Frederick?

  • If you're driving, just take Interstate 70 or Interstate 270 to reach the city. If you prefer public transportation, there are bus services that run from major cities like Baltimore and Washington D.C. to the nearby city of Hagerstown. From there, you can take a taxi or rideshare service to reach your accommodations.
  • If you're flying into the area, the closest airport is Baltimore/Washington International Thurgood Marshall Airport, which is about an hour away by car. You can also fly into Ronald Reagan Washington National Airport or Dulles International Airport, which are both about 90 minutes away by car.
Cheap Flights to Frederick

Discover Maryland's Best in 3 Days, 2 Nights!

Maryland Science Center

Maryland Science Center / Source: Trip.com

Are you ready for a fun-filled 3-day, 2-night trip to Maryland? Get ready to explore some of the state's top destinations and make memories that will last a lifetime. From historic cities to scenic parks, there's something for everyone on this adventure-packed itinerary. So pack your bags, grab your friends, and get ready for an unforgettable journey through the Old Line State!

Day 1: Baltimore and Annapolis

👉 Start your journey in the vibrant city of Baltimore, known for its delicious seafood, rich history, and lively nightlife. Here are some must-see attractions to check out:

  • Visit the historic Inner Harbor and see the USS Constellation, a 19th-century naval warship.
  • Explore the American Visionary Art Museum, showcasing some of the country's most unique and unconventional art pieces.
  • Grab lunch at Faidley's Seafood, a Baltimore institution famous for its crab cakes.
  • Take a scenic drive to Annapolis, Maryland's charming state capital known for its colonial architecture and maritime heritage.
  • Visit the United States Naval Academy and see where the country's future Navy and Marine Corps officers are trained.
  • Enjoy dinner at one of Annapolis' many seafood restaurants, such as O'Learys Seafood Restaurant or Cantler's Riverside Inn.

Day 2: Assateague Island and Ocean City

👉 On day 2, venture out to the eastern shore of Maryland to visit two of the state's most beautiful coastal destinations: Assateague Island and Ocean City.

  • Start your day by visiting Assateague Island National Seashore, where you can see wild horses roaming on the beach and enjoy a peaceful morning walk.
  • Drive down to Ocean City, known for its beautiful beaches and lively boardwalk.
  • Rent bikes or take a stroll down the boardwalk, where you'll find amusement park rides, arcade games, and plenty of food options.
  • Spend the afternoon soaking up the sun on the beach, playing volleyball, or trying out some water sports.
  • Have dinner at one of Ocean City's many seafood restaurants, such as Phillips Seafood or The Crab Bag.

Day 3: St. Michaels and Easton

👉 On your final day in Maryland, head to the charming town of St. Michaels on the eastern shore, known for its quaint shops, seafood restaurants, and historic attractions.

  • Visit the Chesapeake Bay Maritime Museum and learn about the region's rich maritime heritage.
  • Take a stroll down St. Michaels' main street, where you'll find plenty of local shops selling handmade crafts and souvenirs.
  • Enjoy lunch at one of St. Michaels' many seafood restaurants, such as Limoncello or The Crab Claw.
  • Drive to nearby Easton, known for its beautiful parks and historic homes.
  • Visit the Avalon Theatre, a beautifully restored Art Deco theater that hosts live music and events throughout the year.
  • End your trip with dinner at the Bartlett Pear Inn, a historic inn known for its farm-to-table cuisine.
With this itinerary, you're sure to have an unforgettable 3-day, 2-night trip to Maryland. From the bustling city of Baltimore to the tranquil beaches of Ocean City, there's something for everyone to enjoy. So pack your bags and get ready for an adventure through the Old Line State!

FAQ: Everything You Need to Know About Weekend Getaways in Maryland

  • What are some popular weekend getaway destinations in Maryland?

    Maryland is home to a variety of popular weekend getaway destinations, including Baltimore, Annapolis, Chesapeake Bay, Assateague Island, Deep Creek Lake, Ocean City, St. Michaels, and Frederick.

  • What is the best time of year to plan a weekend getaway in Maryland?

    The best time to plan a weekend getaway in Maryland depends on what you're looking for. Spring and fall offer mild temperatures and beautiful foliage, while summer is perfect for outdoor activities and beach trips. Winter is great for cozy getaways and indoor attractions.

  • Are there any outdoor activities to do in Maryland during a weekend getaway?

    Yes, Maryland offers plenty of outdoor activities during a weekend getaway. You can go hiking, biking, kayaking, fishing, or simply take a stroll through one of the many state parks.

  • What types of accommodations are available for weekend getaways in Maryland?

    Maryland has a variety of accommodations available for weekend getaways, including hotels, bed and breakfasts, rental homes, and cabins. Depending on your preference, you can find options ranging from luxurious to budget-friendly.

  • Can you recommend any unique and off-the-beaten-path destinations for a weekend getaway in Maryland?

    If you're looking for a unique and off-the-beaten-path destination for a weekend getaway in Maryland, consider visiting Havre de Grace. This charming town is situated at the mouth of the Susquehanna River and offers beautiful views, delicious seafood, and a rich history.
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