3-Day Scenic Road Trip from Waldorf, MD: Fun and Relaxation Within 5 Hours

Day 1: Historic Charm

Frederick, MD on June 16, 2025

8:00am

Breakfast at The Wandering Frog Café

Start your day with a lovely breakfast at this cozy spot known for rich coffee and fresh-baked pastries, perfect to fuel your day.
USD15, 1h0m

9:30am

Historic Downtown Frederick Walking Tour

Explore the vibrant historic district filled with charming shops, art galleries, and Civil War landmarks. The tour highlights Frederick’s rich history and architecture.
USD0, 2h0m

12:00pm

Lunch at Brewer’s Alley

Enjoy a craft beer paired with gourmet pub food at one of Frederick’s most popular brewpubs, known for its lively atmosphere and local flavors.
USD20, 1h0m

1:30pm

Monocacy National Battlefield

Visit this Civil War battlefield park to learn about the Battle of Monocacy and enjoy walking trails surrounded by scenic nature.
USD0, 1h30m

3:30pm

Drive to Harper's Ferry, WV

Depart for Harper’s Ferry, a scenic one-hour drive west, enjoying the gradual transition from cityscape to river and mountain views.
USD0, 1h0m

5:00pm

Dinner at The Anvil Restaurant

Dine in this historic and cozy restaurant located in Harper’s Ferry, offering hearty American cuisine with an emphasis on local ingredients.
USD30, 1h0m
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Day 2: Scenic Outdoors

Harper's Ferry, WV on June 17, 2025

7:30am

Breakfast at The Country Cafe

Enjoy a hearty homemade breakfast at this popular local spot known for fresh ingredients and friendly service.
USD15, 1h0m

9:00am

Hiking in Harper's Ferry National Historical Park

Spend the morning hiking scenic trails like the Maryland Heights Trail, offering panoramic views of the Potomac and Shenandoah rivers and historic sites.
USD0, 3h0m

12:30pm

Lunch at Potomac Grille

Taste regional fare with stunning river views and relaxed atmosphere inside the park area.
USD25, 1h0m

2:00pm

Explore Harper’s Ferry Town

Stroll the quaint streets to visit shops, museums, and historic sites such as John Brown’s Fort and the Appalachian Trail Conservancy Visitor Center.
USD10, 2h0m

4:30pm

Drive to Annapolis, MD

Head east about 2 hours toward Annapolis, enjoying scenic country roads along the way.
USD0, 2h0m

6:30pm

Dinner at Chick & Ruth’s Delly

Relish casual local favorites in this beloved Annapolis deli known for large portions and inventive sandwiches.
USD20, 1h0m
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Day 3: Waterfront & History

Annapolis, MD on June 18, 2025

8:00am

Breakfast at Miss Shirley’s Café

Enjoy a flavorful, southern-inspired breakfast with options ranging from shrimp and grits to creative pancakes, perfect to start your day by the harbor.
USD20, 1h0m

9:30am

United States Naval Academy Tour

Explore the historic grounds and learn about the Naval Academy’s traditions on a guided tour available daily, booking in advance recommended.
USD0, 2h0m

11:30am

Walk Along City Dock

Enjoy a leisurely walk through Annapolis’s waterfront area with shops, galleries, and charming boats docked in the harbor.
USD0, 1h0m

12:30pm

Lunch at Cantler’s Riverside Inn

Savor fresh Chesapeake Bay crab cakes and seafood at this iconic, casual waterfront restaurant with outdoor seating.
USD30, 1h0m

2:00pm

Drive back to Waldorf, MD

Begin your roughly 1.5-hour drive home, concluding a scenic and fun-packed itinerary.
USD0, 1h30m
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