18‑Day Historic Road‑Trip of the Mid‑Atlantic & New England (May 14 – May 31 2026)

Viewed by 52 travelers

Day 1: Arrival in Washington, D.C.

Morning: Fly with Allegiant Air from Knoxville to Dulles (IAD) and pick up your rental car. Take the scenic Dulles‑Leesburg corridor, avoiding the interstate, to settle into your hotel in the historic Georgetown district.

Afternoon: Stroll along the Georgetown Waterfront and enjoy a leisurely lunch at a riverside café. Use the time to adjust to the time zone and plan the upcoming historic sites.

Evening: Take a relaxed evening walk to the National Mall to view the illuminated monuments. Early dinner at a local tavern sets the tone for the historic adventure.

Book a Hotel

Day 2: Washington, D.C. – Museums & Archives

Morning: Visit the National Archives to see the Declaration of Independence and the Constitution. A guided tour provides context for the documents you’ll encounter later on the road.

Afternoon: Explore the National Museum of American History and the National Museum of Natural History. Both offer interactive exhibits that highlight the nation’s cultural and scientific milestones.

Evening: Dine in the Penn Quarter and enjoy a nightcap at a historic bar that once served politicians and journalists.

Book a Hotel

Day 3: Washington, D.C. – Air, Space & Spy History

Morning: Spend the morning at the National Air and Space Museum, marveling at historic aircraft and spacecraft.

Afternoon: Head to the International Spy Museum for an immersive look at espionage. Afterwards, visit the U.S. Postal Museum to trace the evolution of communication.

Evening: Take a sunset drive on the scenic George Washington Memorial Parkway, avoiding the interstate, and enjoy dinner in Old Town Alexandria.

Book a Hotel

Day 4: Washington, D.C. – Udvar‑Hazy Center & Scenic Departure

Morning: Drive to the Steven F. Udvar‑Hazy Center at Dulles for an extended collection of aircraft, including the Space Shuttle Discovery.

Afternoon: Return to the city via the historic Alexandria Route (Route 7), stopping at historic homes along the Potomac.

Evening: Enjoy a farewell dinner in the vibrant U Street Corridor, then rest for the next day’s journey northward.

Book a Hotel

Day 5: Gettysburg, Pennsylvania

Morning: Depart Washington on the historic Lincoln Highway (U.S. 30) toward Gettysburg National Military Park. The drive offers rolling farmland and Civil War landmarks.

Afternoon: Take a guided battlefield tour, visiting sites such as Little Round Top and the Gettysburg Museum and Visitor Center.

Evening: Dine in the historic downtown and stay overnight in a restored 19th‑century inn.

Book a Hotel

Day 6: Amish Country, Lancaster County

Morning: Travel the scenic Route 222 to the heart of Amish Country. Stop at a local farmer’s market for fresh produce.

Afternoon: Join a horse‑and‑buggy tour, visiting Amish farms and craft shops. Sample homemade pretzels and cheese.

Evening: Enjoy a quiet dinner at a family‑run restaurant before returning to your Lancaster lodging.

Book a Hotel

Day 7: Delaware – First State National Historical Park

Morning: Follow the historic Old Baltimore Pike (MD 281/DE 4) to First State National Historical Park in Dover.

Afternoon: Explore the park’s sites, including the John Dickinson House and the historic courthouse. Take a leisurely walk along the Delaware River trail.

Evening: Stay in a boutique hotel in historic downtown Dover and enjoy a meal featuring local seafood.

Book a Hotel

Day 8: Connecticut – Mystic & New Haven

Morning: Drive the scenic coastal Route 1 through the Delaware‑Pennsylvania border into Connecticut, arriving at Mystic Seaport.

Afternoon: Tour the maritime museum and historic ships, then head to New Haven to see the historic Yale University campus (outside view only).

Evening: Sample New Haven’s famous pizza before checking into a historic inn near the waterfront.

Book a Hotel

Day 9: Plymouth, Massachusetts – Plymouth Rock

Morning: Travel the coastal Route 3A, enjoying ocean views en route to Plymouth Rock and the Plymouth Pilgrim Memorial Museum.

Afternoon: Take a guided walking tour of the historic waterfront, visiting the Mayflower II replica and the historic burial ground.

Evening: Dine at a seaside tavern and stay overnight in a historic colonial‑style B&B.

Book a Hotel

Day 10: Salem, Massachusetts – Witch History

Morning: Drive the scenic By‑Pine Route (MA 1A) to Salem. Begin with the Salem Witch Museum for an engaging overview.

Afternoon: Visit the House of the Seven Gables and the historic Salem Maritime National Historic Site.

Evening: Enjoy a ghost‑walk tour through the historic streets, then retire to a charming inn.

Book a Hotel

Day 11: Ben & Jerry’s Headquarters, Waterbury, Vermont

Morning: Take the scenic Green Mountain By‑way (VT 100) northward to Ben & Jerry’s Headquarters in Waterbury.

Afternoon: Tour the factory, sample limited‑edition flavors, and explore the on‑site scoop shop. Stop at nearby Ben & Jerry’s Ice Cream Scoop Shop in downtown Waterbury.

Evening: Dine at a farm‑to‑table restaurant in Stowe and spend the night in a cozy mountain lodge.

Book a Hotel

Day 12: Scenic Drive to Boston via New Hampshire

Morning: Depart Vermont on Route 2, known as “The Old‑Maine‑Road,” winding through New Hampshire’s White Mountains.

Afternoon: Stop at the historic Portsmouth, New Hampshire waterfront for lunch and a brief walk through Market Square.

Evening: Arrive in Boston, check into a historic hotel in the Beacon Hill district, and enjoy dinner at a classic New England seafood house.

Book a Hotel

Day 13: Boston – Freedom Trail (Part 1)

Morning: Begin the Freedom Trail at Boston Common, visiting the Massachusetts State House and the Park Street Church.

Afternoon: Continue to the Old State House and the Faneuil Hall Marketplace, sampling local treats.

Evening: Take a harbor sunset cruise and dine in the historic North End.

Book a Hotel

Day 14: Boston – Freedom Trail (Part 2)

Morning: Walk to the Paul Revere House and the Old North Church, learning about the midnight ride.

Afternoon: Visit the USS Constitution and the Boston Maritime Museum at the Charlestown Navy Yard.

Evening: Enjoy a performance at the historic Boston Opera House before returning to your hotel.

Book a Hotel

Day 15: Return Journey – Scenic Route Through the Berkshires

Morning: Depart Boston via Route 2A, entering the Berkshires for rolling hills and historic estates.

Afternoon: Stop at the Norman Rockwell Museum in Stockbridge and explore the town’s quaint Main Street.

Evening: Stay overnight in a historic inn in Lenox, enjoying farm‑to‑table cuisine.

Book a Hotel

Day 16: Connecticut River Valley – Historic Towns

Morning: Travel south on the scenic Route 44 along the Connecticut River, visiting Old Saybrook and its historic lighthouse.

Afternoon: Explore the Harriet Beecher Stowe Center in Hartford and the historic Mark Twain House.

Evening: Return to Washington, D.C. via the historic Baltimore–Washington corridor, checking into a boutique hotel near the Capitol.

Book a Hotel

Day 17: Washington, D.C. – Leisure & Last‑Minute Sites

Morning: Revisit any favorite museum or take a guided walking tour of the U.S. Capitol Grounds.

Afternoon: Enjoy a relaxed lunch in the historic Eastern Market and browse local artisans.

Evening: Pack and enjoy a farewell dinner at a classic D.C. steakhouse.

Book a Hotel

Day 18: Departure from IAG Airport

Morning: Transfer to IAG (Washington Dulles) Airport for your return flight. Return the rental car and check‑in.

Afternoon: Flight departs back to Knoxville, concluding the historic road‑trip.

Evening: Arrive home with memories of America’s past and scenic journeys.

Book a Hotel

Time and Cost Estimates

  • National Archives – 2 hrs – $0 (free entry)
  • National Museum of American History – 2 hrs – $0 (free)
  • National Air and Space Museum – 2 hrs – $0 (free)
  • International Spy Museum – 2 hrs – $25
  • U.S. Postal Museum – 1 hr – $0 (free)
  • Steven F. Udvar‑Hazy Center – 3 hrs – $30 (parking $10)
  • Gettysburg National Military Park – 4 hrs – $30 (tour guide)
  • Amish Country Tour – 3 hrs – $20
  • First State National Historical Park – 3 hrs – $0 (free)
  • Mystic Seaport – 3 hrs – $24
  • Plymouth Rock & Pilgrim Memorial Museum – 2 hrs – $10
  • Salem Witch Museum – 2 hrs – $15
  • Ben & Jerry’s Headquarters Tour – 2 hrs – $10 (scoop)
  • Freedom Trail (Boston) – 6 hrs – $0 (free walk)
  • Norman Rockwell Museum – 2 hrs – $20
  • Harriet Beecher Stowe Center – 2 hrs – $12
  • Mark Twain House – 2 hrs – $15
  • U.S. Capitol Grounds Tour – 2 hrs – $0 (free)
  • Rental Car (18 days, scenic routes) – – – $850
  • Flights (Knoxville ↔ Dulles) – – – $350
  • Accommodations (18 nights) – – – $2,160
  • Meals & Miscellaneous – – – $1,200
  • Total Estimated Cost – – – $5,096

Tips

If you need more time to explore the historic sites, consider adding an extra day in Washington, D.C., or extending your stay in Boston to include the nearby historic town of Concord. To shorten the trip, you can combine the Connecticut and New Haven stops into a single day and skip the Berkshires, reducing the itinerary by two days while still hitting the major landmarks.

0