Welcome to “America in Miniature,” a state where towering mountains, historic cities, and serene coastal towns are all just a short drive away. Whether you’re planning a romantic escape, a family adventure, or a solo retreat, Maryland offers an incredible diversity of destinations perfect for a quick escape. This guide is your key to planning the best Maryland weekend trips for 2025. We’ve curated a list of 15 unique Maryland vacation spots, each offering its own distinct charm and activities. From the bustling Inner Harbor of Baltimore to the wild horses of Assateague Island, these short getaways in Maryland provide the perfect break from the everyday.
Plan Your Perfect Maryland Getaway
1. Annapolis: The Sailing Capital
A historic treasure trove, Annapolis charms visitors with its colonial architecture, maritime heritage, and lively waterfront. As Maryland’s capital, it offers a perfect blend of history, culture, and relaxation.
- Top Attractions: Explore the U.S. Naval Academy, tour the Maryland State House (the oldest in continuous legislative use), stroll along the City Dock’s “Ego Alley,” and take a sailing cruise on the Chesapeake Bay. The William Paca House & Garden offers a glimpse into 18th-century life.
- Accommodations & Price Ranges: Stay in historic inns or modern hotels. Budget: ($150-$235) options like the Hampton Inn. Mid-Range: ($220-$400) at historic B&Bs like the Flag House Inn or Governor Calvert House. Luxury: ($400+) at waterfront properties like the Annapolis Waterfront Hotel.
- Dining Scene: Annapolis is a seafood lover’s paradise. Enjoy world-class crab cakes at Boatyard Bar & Grill or fresh oysters at Sailor Oyster Bar.
- Best Time to Visit: Spring and fall offer pleasant weather for walking tours and sailing. The city is especially beautiful during the October boat shows.
- Budget Considerations: Many historic sites, including the State House, offer free tours. Enjoy a low-cost afternoon watching the boats at City Dock.
- Travel Tips & Accessibility: Downtown Annapolis is highly walkable. Use the free pink-purple shuttle bus to navigate between key areas.
2. Ocean City: The Classic Beach Escape
With 10 miles of sandy beaches and a three-mile boardwalk packed with amusements, shops, and treats, Ocean City is the ultimate destination for a fun-filled coastal getaway.
- Top Attractions: Walk the iconic Ocean City Boardwalk, ride the Ferris wheel at Trimper’s Rides, cool off at Jolly Roger Amusement Park, and enjoy a day of sunbathing and swimming.
- Accommodations & Price Ranges: A wide range of options are available. Budget: ($40-$110) at motels like the Cabana Motel. Mid-Range: ($110-$250) at hotels like the Grand Hotel or Holiday Inn. Luxury: ($250-$400+) in oceanfront suites at resorts like the Hilton Garden Inn.
- Dining Scene: From fresh seafood at The Crab Bag to classic boardwalk fare like Thrasher’s French Fries, there’s something for every palate.
- Best Time to Visit: Late May to early September is peak season for beach weather. Visit in the spring or fall for popular events like Springfest and Sunfest with fewer crowds.
- Budget Considerations: The beach and boardwalk are free to access. Look for vacation rental deals, with some condos starting around $84 per night.
- Travel Tips & Accessibility: Use the Boardwalk Tram or the city bus to get around easily. Book accommodations well in advance for summer visits.
3. Deep Creek Lake: The Mountain Adventure
Nestled in the mountains of Western Maryland, Deep Creek Lake is a year-round playground for outdoor enthusiasts. It’s the state’s largest freshwater lake and a hub for adventure.
- Top Attractions: Enjoy boating, fishing, and swimming in the summer. In winter, hit the slopes for skiing and snowboarding at Wisp Resort. Hike to Muddy Creek Falls in Swallow Falls State Park, one of Maryland’s most beautiful waterfalls.
- Accommodations & Price Ranges: Cabins and vacation rentals are popular here. Budget: ($150-$300) for smaller cabins or off-lake rentals. Mid-Range: ($300-$550) for lake-access homes with amenities like hot tubs. Luxury: ($550+) for large, lakefront properties with private docks.
- Dining Scene: Enjoy a meal with a view at Firewater Kitchen & Bar or grab a casual bite at Brenda’s Pizzeria.
- Best Time to Visit: Summer is ideal for water sports, while fall offers breathtaking foliage during the Autumn Glory Festival in October. Winter is perfect for skiing.
- Budget Considerations: State parks offer low-cost entry for hiking and picnicking. Visiting during the spring shoulder season can yield lower rental prices.
- Travel Tips & Accessibility: A car is essential for exploring the area. The region is celebrating its 100th anniversary in 2025, so expect special events.
4. Baltimore: The Vibrant Charm City
Baltimore offers a dynamic urban escape with a rich history, world-class museums, and diverse neighborhoods, all centered around its famous Inner Harbor.
- Top Attractions: Visit the National Aquarium, explore the historic ships docked in the Inner Harbor, climb Federal Hill for panoramic city views, and catch an Orioles game at Camden Yards. The American Visionary Art Museum and Fort McHenry are also must-sees.
- Accommodations & Price Ranges: Budget: ($85-$150) at hotels like the Days Inn by Wyndham Inner Harbor. Mid-Range: ($150-$250) at properties like the Renaissance Baltimore Harborplace Hotel. Luxury: ($250-$480+) at the Four Seasons or Sagamore Pendry Baltimore.
- Dining Scene: Savor Maryland blue crabs at L.P. Steamers, explore the diverse food stalls at Lexington Market, or enjoy upscale dining in the Harbor East neighborhood.
- Best Time to Visit: Spring and fall offer pleasant weather for exploring the city’s walkable neighborhoods.
- Budget Considerations: Walk around the Inner Harbor, visit the Rawlings Conservatory in Druid Hill Park for free, or use the free Charm City Circulator bus.
- Travel Tips & Accessibility: The Inner Harbor is very walkable. The Water Taxi is a fun and scenic way to travel between neighborhoods like Fells Point and Federal Hill.
5. St. Michaels: The Quaint Maritime Town
Known for its maritime history and serene atmosphere, St. Michaels is a picturesque town on the Eastern Shore that’s perfect for a relaxing and romantic getaway.
- Top Attractions: Immerse yourself in history at the Chesapeake Bay Maritime Museum, which features a working boatyard and the 1879 Hooper Strait Lighthouse. Take a scenic cruise on the Miles River, browse the boutique shops on Talbot Street, or rent a kayak.
- Accommodations & Price Ranges: Budget: ($150-$200) at inns like the St. Michaels Inn. Mid-Range: ($200-$350) at boutique hotels like The Wildset Hotel. Luxury: ($350+) at the renowned Inn at Perry Cabin, which offers a spa, golf, and waterfront dining.
- Dining Scene: Enjoy casual crab feasts at The Crab Claw or innovative, upscale cuisine at Ruse.
- Best Time to Visit: Late spring through early fall is ideal, when the weather is perfect for water activities and outdoor dining. The town hosts popular festivals like WineFest and OysterFest.
- Budget Considerations: Enjoy a picnic in Muskrat Park or simply stroll through the historic streets to admire the architecture.
- Travel Tips & Accessibility: The town is very walkable and bike-friendly. It’s a popular destination, so book accommodations and dinner reservations in advance.
6. Frederick: The Historic Crossroads
With a 50-block historic district, a thriving arts scene, and proximity to Civil War battlefields, Frederick offers a culturally rich weekend getaway with a modern, creative vibe.
- Top Attractions: Explore the National Museum of Civil War Medicine, walk the scenic Carroll Creek Park, visit the Monocacy National Battlefield, and browse the unique shops and art galleries downtown.
- Accommodations & Price Ranges: Budget: ($100-$160) at chain hotels on the outskirts of the historic district. Mid-Range: ($160-$250) at charming B&Bs like 10 Clarke Place. Luxury: ($250+) at upscale inns or boutique hotels like the Visitation Hotel.
- Dining Scene: Frederick’s food scene is booming. Enjoy farm-to-table dining at The Wine Kitchen on the Creek or grab a craft beer at one of the many local breweries like Attaboy Barrel House.
- Best Time to Visit: Year-round, but fall is especially beautiful for trips to nearby orchards and wineries. Summer features events like Alive @ Five.
- Budget Considerations: Strolling through Carroll Creek Park and the historic district is a great free activity.
- Travel Tips & Accessibility: The historic downtown is very walkable. For a car-free trip, take the MARC train from Washington, D.C., on weekends.
7. Assateague Island: The Wild Escape
For a truly unique nature-focused getaway, head to Assateague Island, a protected barrier island famous for the wild horses that roam its beaches and marshes.
- Top Attractions: The main attraction is spotting the wild horses. Other activities include beachcombing, birdwatching, kayaking, and camping under the stars. Hike the Life of the Marsh and Life of the Dunes nature trails.
- Accommodations & Price Ranges: Camping is the most popular option. Budget: ($30 per night) for a rustic campsite at Assateague Island National Seashore. Mid-Range: ($100-$200) at nearby hotels in Ocean City or Berlin.
- Dining Scene: There are no restaurants on the island. Pack a picnic or drive to nearby towns like Berlin or Ocean City for meals.
- Best Time to Visit: Spring and fall offer pleasant weather, fewer insects, and smaller crowds. You might even see newborn foals in the spring.
- Budget Considerations: Camping is an affordable way to stay. The entrance fee to the National Seashore is valid for seven days.
- Travel Tips & Accessibility: Always keep a distance of at least 40 feet (a bus length) from the wild horses. Secure all food in your vehicle or a horse-proof container. Insect repellent is a must, especially in summer.
8. National Harbor: The Waterfront Resort
Located on the Potomac River just south of Washington, D.C., National Harbor is a vibrant resort destination with shopping, dining, and entertainment for all ages.
- Top Attractions: Ride The Capital Wheel for stunning panoramic views, watch a free movie on the waterfront plaza screen, explore the massive Gaylord National resort, and try your luck at the MGM National Harbor casino. Don’t miss the iconic “The Awakening” sculpture on the beach.
- Accommodations & Price Ranges: Mid-Range: ($150-$250) at hotels like the Hyatt Place. Luxury: ($250-$500+) at the Gaylord National Resort & Convention Center or MGM National Harbor.
- Dining Scene: The area boasts a wide variety of restaurants, from upscale steakhouses like Old Hickory to casual spots like Rosa Mexicano.
- Best Time to Visit: Summer brings outdoor concerts and movies, while the holiday season features the spectacular “Christmas on the Potomac” celebration.
- Budget Considerations: Enjoy free events like summer concerts and fireworks. Strolling the waterfront and window shopping costs nothing.
- Travel Tips & Accessibility: National Harbor is very walkable. Water taxis provide a scenic connection to Alexandria, Virginia, and The Wharf in D.C.
9. Chesapeake City: The Canal Town Charm
This picturesque town is the only one in Maryland situated directly on a working commercial canal—the Chesapeake and Delaware Canal. Its south side is a beautifully preserved 19th-century historic district.
- Top Attractions: Visit the C&D Canal Museum to learn about the waterway’s history, walk or bike along the Ben Cardin Recreational Trail, and watch massive container ships pass through the canal. Enjoy a narrated boat tour for a unique perspective.
- Accommodations & Price Ranges: Stay in historic B&Bs. Mid-Range: ($150-$250) at charming spots like the Inn at the Canal or the Blue Max Inn.
- Dining Scene: Enjoy waterfront dining at the Chesapeake Inn Restaurant & Marina or Schaefer’s Canal House.
- Best Time to Visit: Summer and fall are perfect for enjoying the waterfront and outdoor dining. The town hosts a festive Candlelight House Tour in December.
- Budget Considerations: Exploring the historic district on foot is free, as is watching the ships from Pell Gardens.
- Travel Tips & Accessibility: The historic south side is compact and easy to explore on foot. A small ferry can take you across the canal to the north side.
10. Tilghman Island: The Authentic Waterman’s Village
For an authentic taste of Chesapeake Bay life, visit Tilghman Island, a working waterman’s village where fishing, crabbing, and oystering are still a way of life.
- Top Attractions: Learn about local heritage at the Tilghman Watermen’s Museum, charter a fishing boat for a day on the bay, or take a sail on a historic skipjack like the Rebecca T. Ruark.
- Accommodations & Price Ranges: Mid-Range: ($180-$310) at inns like Knapp’s Narrows Marina and Inn. Luxury: ($300+) at the Wylder Hotel Tilghman Island, which offers a pool, marina, and crab shack.
- Dining Scene: It’s all about fresh seafood here. Enjoy crab cakes and rockfish at waterfront restaurants like Tickler’s Crab Shack.
- Best Time to Visit: Visit in the fall for Tilghman Island Day in October, a celebration of local culture with boat docking contests and fresh oysters.
- Budget Considerations: The island’s natural beauty is free to enjoy. Pack a lunch and have a picnic at Black Walnut Point.
- Travel Tips & Accessibility: The island is small and best explored by bike or on foot. It’s a quiet, laid-back destination perfect for unplugging.
11. Berlin: America’s Coolest Small Town
Named “America’s Coolest Small Town” by Budget Travel, Berlin is a historic gem just minutes from Ocean City and Assateague. Its charming Main Street is lined with unique shops, galleries, and restaurants.
- Top Attractions: Stroll down the historic Main Street, featured in films like Runaway Bride. Visit the quirky Mermaid Museum, browse the art galleries, and explore the Calvin B. Taylor House Museum.
- Accommodations & Price Ranges: Mid-Range: ($150-$250) at historic inns like The Atlantic Hotel or The Inn Berlin.
- Dining Scene: Enjoy a meal at The Globe Theater, a historic venue turned restaurant, or sample local brews at Burley Oak Brewing Company.
- Best Time to Visit: Year-round, with fun events like the Bathtub Races in July, the Peach Festival in August, and a festive Christmas celebration.
- Budget Considerations: Window shopping and strolling through the historic streets are delightful and free activities.
- Travel Tips & Accessibility: Berlin is a great home base for exploring both Ocean City and Assateague Island without staying in the busiest areas.
12. Havre de Grace: The Bay’s Northern Jewel
Situated where the Susquehanna River meets the Chesapeake Bay, Havre de Grace is a waterfront town rich in maritime history and natural beauty.
- Top Attractions: Walk the scenic Promenade along the water to the Concord Point Lighthouse, the oldest publicly accessible lighthouse in Maryland. Explore the Decoy Museum and the Maritime Museum to learn about the area’s heritage.
- Accommodations & Price Ranges: Mid-Range: ($150-$220) at B&Bs like the Spencer-Silver Mansion or Vandiver Inn.
- Dining Scene: Enjoy fresh seafood with a view at MacGregor’s Restaurant & Tavern or WaterStreet Seafood.
- Best Time to Visit: Summer is perfect for boating and enjoying the waterfront. The town hosts a popular Seafood Festival in August.
- Budget Considerations: The Promenade and Concord Point Lighthouse are free to visit.
- Travel Tips & Accessibility: The waterfront and downtown historic district are easily walkable.
13. Chesapeake Beach: The Bayfront Resort Town
Once a bustling early 20th-century resort connected to Washington, D.C., by railway, Chesapeake Beach today is a relaxing bayfront town perfect for families.
- Top Attractions: Hunt for shark teeth and fossils at Breezy Point Beach, splash around at the Chesapeake Beach Water Park, and learn about local history at the Chesapeake Beach Railway Museum. Walk or bike the scenic Chesapeake Beach Railway Trail.
- Accommodations & Price Ranges: Mid-Range: ($150-$300) at resorts like the Rod ‘N’ Reel, which offers rooms, dining, and charter fishing.
- Dining Scene: Enjoy waterfront dining and fresh seafood at the restaurants connected to the Rod ‘N’ Reel Resort.
- Best Time to Visit: Summer is the best time to enjoy the water park and beaches.
- Budget Considerations: Breezy Point Beach has a modest admission fee and offers a full day of fun.
- Travel Tips & Accessibility: Chesapeake Beach and its neighbor, North Beach, are often visited together and offer a classic, family-friendly bay experience.
14. Salisbury: The Eastern Shore’s Hub
As the largest city on the Eastern Shore, Salisbury serves as a fantastic hub for exploring the entire region, with its own set of charming attractions.
- Top Attractions: Visit the Salisbury Zoological Park (with free admission!), explore the Ward Museum of Wildfowl Art, and take a stroll through the historic Pemberton Historical Park.
- Accommodations & Price Ranges: Budget: ($100-$150) at reliable chain hotels. Mid-Range: ($150-$220) at hotels with more amenities or B&Bs in the surrounding area.
- Dining Scene: Sample local craft beer and food at Evolution Craft Brewing Company or enjoy a meal in the revitalized downtown area.
- Best Time to Visit: Fall is a great time to visit for events like the Sea Gull Century bike ride. The Maryland Folk Festival is often held here in late summer.
- Budget Considerations: The Salisbury Zoo is a top-tier free attraction, perfect for families.
- Travel Tips & Accessibility: Use Salisbury as your basecamp for day trips to Ocean City, Assateague Island, and the Blackwater National Wildlife Refuge.
15. Easton: The Cultural Heart of the Shore
Easton is a sophisticated and historic town that serves as a cultural hub for the Eastern Shore, known for its art galleries, theaters, and colonial architecture.
- Top Attractions: Visit the Academy Art Museum, catch a show at the historic Avalon Theatre, and browse the upscale boutiques and antique shops downtown.
- Accommodations & Price Ranges: Mid-Range: ($170-$250) at hotels like the Tidewater Inn. Luxury: ($250+) at historic inns and upscale B&Bs.
- Dining Scene: Easton has a refined dining scene with options ranging from casual cafes to fine dining establishments.
- Best Time to Visit: Fall is the prime season, especially during the Waterfowl Festival in November, a massive event celebrating the region’s wildlife and art.
- Budget Considerations: Enjoy the beautiful architecture on a self-guided walking tour of the historic district.
- Travel Tips & Accessibility: Easton’s compact downtown is perfect for exploring on foot. It’s an excellent stop on a scenic driving loop of the Eastern Shore.
Your Maryland Adventure Awaits
From the mountains to the sea, Maryland is packed with incredible destinations that are perfect for a weekend escape in 2025. Each spot offers a unique slice of the state’s history, culture, and natural beauty. Whether you’re seeking adventure, relaxation, or a bit of both, you’ll find it here.
Now it’s your turn! What are your favorite Maryland weekend trips? Share your top spots or the destination you’re most excited to visit in the comments below. Happy travels
