10 Maryland Road Trip Ideas With Hidden Gems

Maryland may be one of the smallest states in the U.S., but it’s full of road trip worthy adventures. From misty mountains and historic towns to quiet beaches and coastal wildlife, the state offers a surprising range of landscapes. Whether you want a peaceful weekend escape or a full-on exploration of hidden natural beauty, Maryland’s backroads and byways are packed with scenic gems, charming stops, and underrated treasures. Below are ten unforgettable Maryland road trip ideas that combine well known highlights with tucked-away spots locals love.

10. Chesapeake Bay Coastal Loop

This scenic road trip hugs the coastline of the Chesapeake Bay and explores Maryland’s iconic Eastern Shore. Start in historic Annapolis, where you can stroll cobblestone streets and enjoy fresh seafood, then head into the heart of the Eastern Shore for a laid-back mix of marinas, small-town charm, and coastal heritage. Visit St. Michaels, Oxford, and Tilghman Island for a slower pace, beautiful water views, and maritime culture. Along the way, you’ll discover quiet parks, sleepy harbors, and preserved colonial-era landmarks.

Ideal Time to Go:
May through October for mild weather and waterfront dining.

Hidden Gems to See:

• Ferry ride from Oxford to Bellevue

• Tilghman Island’s working watermen harbors

• Poplar Island restoration tours

• Terrapin Nature Park (quiet beach walk)

• Blackwater National Wildlife Refuge

Sample Itinerary:
Day 1: Annapolis, St. Michaels
Day 2: Oxford, Tilghman Island
Day 3: Blackwater National Wildlife Refuge, Cambridge, return via Route 50

9. Western Maryland Mountains Loop

Escape into the Appalachian highlands with this road trip through Garrett and Allegany Counties in far western Maryland. The area is home to scenic lakes, state parks, and forest trails ideal for outdoor lovers. Deep Creek Lake offers boating, swimming, and skiing, but surrounding gems like Cranesville Swamp and Savage River State Forest provide solitude and ecological diversity. This route is especially stunning in fall, when the leaves turn the entire landscape into a canvas of red, orange, and gold. If you enjoy sights like this, also consider visiting the greater Blue Ridge Mountains close by after!

Ideal Time to Go:
Late September through October for peak fall foliage.

Hidden Gems to See:

• Casselman River Bridge State Park

• Meadow Mountain firetower views

• Cranesville Swamp Preserve boardwalk

• New Germany State Park

• Secret coves at Deep Creek Lake

Sample Itinerary:
Day 1: Deep Creek Lake, Swallow Falls State Park
Day 2: Cranesville Swamp, Frostburg
Day 3: Savage River State Forest, return via I-68

8. Civil War History & Nature Tour

Pair historic landmarks with scenic hiking trails in this central Maryland road trip. Visit the Antietam National Battlefield, where one of the Civil War’s bloodiest days took place. Then stretch your legs on the Appalachian Trail or enjoy the calm shores of Greenbrier Lake. The mix of history and nature makes this a balanced itinerary for both learning and outdoor adventure.

Ideal Time to Go:
Spring and fall for cool, dry hiking weather.

Hidden Gems to See:

• Devil’s Backbone Park (historic stone bridge)

• Annapolis Rock overlook (sunset view)

• Greenbrier State Park lake trail

• South Mountain’s lesser-used side trails

Sample Itinerary:
Day 1: Antietam Battlefield, Shepherdstown
Day 2: Appalachian Trail, Annapolis Rock (photo above)
Day 3: Cunningham Falls, Greenbrier State Park

7. Assateague Island and Eastern Shore Adventure

Venture to Maryland’s Atlantic coast and discover one of the most unique landscapes in the state. Assateague Island National Seashore is home to wild ponies, rolling sand dunes, and untouched beaches and it is one of the coolest East Coast National Parks to explore. Beyond the popular parts of the park, there are hidden trails, quiet kayaking routes, and small towns like Berlin that transport you back in time. This road trip blends beach relaxation with coastal wildlife encounters.

Ideal Time to Go:
Late spring to early fall for swimming, kayaking, and pony spotting.

Hidden Gems to See:

• Life of the Dunes trail

• Town of Berlin (antique shops and history)

• Pocomoke River State Park kayak trails

• Rackliffe Plantation House

• Assateague sunrise walks

Sample Itinerary:
Day 1: Berlin, Assateague beach trails
Day 2: Pocomoke River kayaking, Snow Hill
Day 3: Sunrise at Assateague, visit Rackliffe Plantation

6. Baltimore to Ellicott City Cultural Drive

Explore the artistic and historical treasures of central Maryland with this short but packed road trip. Start in Baltimore to experience its revitalized neighborhoods, quirky art scenes, and iconic harbor. Then head to Ellicott City, where centuries-old architecture meets riverside trails and artisan shops. The contrast between urban buzz and historic quiet makes for a refreshing combination.

Ideal Time to Go:
Year-round, but spring and fall offer comfortable weather.

Hidden Gems to See:

• Graffiti Alley (free street art zone)

• Cylburn Arboretum

• Trolley trail in Ellicott City

• Mill ruins near Patapsco River

Sample Itinerary:
Day 1: Inner Harbor, Graffiti Alley, Hampden
Day 2: Ellicott City Main Street, Patapsco Valley hiking

5. Southern Maryland Wine & Waterways Tour

This road trip offers a peaceful escape through Southern Maryland’s farmland, vineyards, and riverside towns. Visit Calvert Cliffs for fossil hunting and scenic hiking, then head to the Patuxent River for waterfront dining and kayaking. Enjoy a slower pace as you sip wine at hillside wineries and explore the colonial-era history at St. Mary’s City.

Ideal Time to Go:
May through October for beach access and winery events.

Hidden Gems to See:

• Fossil beaches at Flag Ponds

• Jefferson Patterson Park trails

• Slack Winery’s scenic patio

• Historic St. Mary’s City (living history site)

Sample Itinerary:
Day 1: Calvert Cliffs, Jefferson Patterson Park
Day 2: Flag Ponds, wineries, Solomon’s Island
Day 3: Historic St. Mary’s City

4. Harford County Countryside Loop

Harford County in northeast Maryland is home to rolling farmland, charming small towns, and scenic state parks. A drive through this region offers peaceful scenery, hidden waterfalls, and historical lighthouses. It’s perfect for a weekend getaway away from the city crowds.

Ideal Time to Go:
Late spring through early fall.

Hidden Gems to See:

• Kilgore Falls

• Liriodendron Mansion

• Susquehanna State Park’s stone mill ruins

• Concord Point Lighthouse at sunrise

Sample Itinerary:
Day 1: Kilgore Falls, Rocks State Park
Day 2: Havre de Grace, Susquehanna State Park

3. Historic Towns of Frederick County

Frederick County blends Maryland’s rich colonial history with its scenic countryside. Start in downtown Frederick with its lively shops, creekside art walk, and Civil War heritage. Then head to the countryside to explore covered bridges, furnace ruins, and forest hikes. This route is ideal for history buffs and photographers alike.

Ideal Time to Go:
Any time of year, but fall offers the best colors and festivals.

Hidden Gems to See:

• Roddy Road and Utica Covered Bridges

• Catoctin Furnace trail

• Carroll Creek Park murals

• Monocacy Battlefield walking trails

Sample Itinerary:
Day 1: Frederick’s downtown and creek walk
Day 2: Covered bridges drive, Catoctin Furnace

2. Bay to Boardwalk Mini Coastal Drive

Skip Ocean City crowds and take this quieter coastal route from Chesapeake Beach to the southern tip of Maryland’s western shore. Along the way, explore quiet boardwalks, peaceful bays, and Civil War sites by the water. This is a great trip for nature lovers who want the beach experience without the noise.

Ideal Time to Go:
Summer and early fall.

Hidden Gems to See:

• Breezy Point Beach (local favorite)

• North Beach’s laid-back boardwalk

• Flag Ponds Nature Park

• Point Lookout Civil War ruins

Sample Itinerary:
Day 1: Chesapeake Beach, Breezy Point
Day 2: Flag Ponds, Point Lookout State Park

1. Scenic Byways and Nature Trails of Montgomery County

Just outside of Washington, D.C., Montgomery County hides beautiful farmland, wineries, forest trails, and scenic overlooks. This route winds through Barnesville, Sugarloaf Mountain, and Poolesville for a rural retreat filled with charm and relaxation. It’s a perfect day trip or overnight escape.

Ideal Time to Go:
Spring and fall, especially for winery visits and wildflower hikes.

Hidden Gems to See:

• Sugarloaf Mountain overlook

• Rocklands Farm Winery

• Barnesville countryside loop

• Little Bennett Regional Park

Sample Itinerary:
Day 1: Sugarloaf Mountain hike, winery visit
Day 2: Little Bennett Regional Park, Barnesville backroads

Maryland Road Trip Packing List

• Comfortable walking shoes and hiking boots

• Daypack for trails

• Sunscreen and bug spray

• Reusable water bottles

• Maryland State Park pass

• Camera or smartphone with storage

• Lightweight jacket or rain layer

• Offline maps or GPS backup

Things to Know Before You Go

• Some parks charge small entrance fees, bring cash or check availability online.

• Maryland weather can shift quickly, check forecasts before you go.

• Cell service may be spotty in remote areas; download maps ahead of time.

• Pack for both outdoor adventure and casual town stops (restaurants, museums).

• Always check park websites for seasonal closures or special events.

Final Thoughts

From wild ponies on the coast to mountain hikes in the west, Maryland offers more variety than most expect. Whether you’re after beach views, historic landmarks, or quiet forests, these road trip ideas provide something for every kind of explorer. Add a few of these hidden gems to your itinerary and see a side of Maryland you won’t find in guidebooks.

Have any questions or suggestions for more hidden gems in Maryland? Drop them in the comments below, I’d love to hear from you!

Related:

• Pennsylvania road trip ideas
• Michigan road trip ideas
• Ohio road trip ideas