Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

18‑Day Historic Road‑Trip from Washington, D.C. to New England (May 14 – June 1 2026)

Viewed by 211 travelers

Day 1: Arrival & Orientation in Washington, D.C.

Morning: Arrive on Allegiant Air at Dulles Airport and pick up your rental car. Take a quick coffee break at a nearby café while reviewing the road‑trip itinerary.

Afternoon: Check into your downtown hotel and enjoy a leisurely stroll along the National Mall, getting your first glimpse of the iconic monuments.

Evening: Dine at a historic tavern in Georgetown and rest up for a museum‑filled day tomorrow.

Find Hotels

Day 2: Washington, D.C. – Museum Marathon

Morning: Visit the National Archives to see the Declaration of Independence and the Constitution; allocate about 2 hours.

Afternoon: Head to the National Museum of American History and the National Air and Space Museum on the Mall, spending roughly 3 hours total.

Evening: Explore the International Spy Museum for 2 hours, then enjoy a rooftop dinner with city views.

**Day 3: Washington, D.C. – More Cultural Gems**

Morning: Tour the National Postal Museum (1.5 hours) and admire its historic artifacts.

Afternoon: Take the short drive to the Udvar‑Hazy Center at Dulles for the giant aircraft displays (2 hours).

Evening: Relax at the hotel or catch a performance at the Kennedy Center.

Find Hotels

Day 4: Scenic Drive to Gettysburg, PA

Morning: Depart Washington on Route 7, enjoying countryside views and avoiding interstates.

Afternoon: Arrive at the Gettysburg National Military Park, take a guided battlefield tour (3 hours).

Evening: Dine in downtown Gettysburg and settle into a historic inn.

Find Hotels

Day 5: Gettysburg to Lancaster Amish Country

Morning: Explore the Gettysburg Museum & Visitor Center for additional context (1.5 hours).

Afternoon: Drive to Lancaster via scenic backroads; arrive in Amish Country and enjoy a buggy ride (2 hours).

Evening: Sample traditional Pennsylvania Dutch cuisine and stay overnight in a bed‑and‑breakfast.

Find Hotels

Day 6: Amish Country to Delaware

Morning: Visit an Amish farm market and the Amish Heritage Center (2 hours).

Afternoon: Continue east on Route 41 and Route 13, crossing into Delaware with scenic stops at historic towns.

Evening: Check into a boutique hotel in Wilmington and walk along the Riverfront.

Find Hotels

Day 7: First State National Historical Park, Delaware

Morning: Explore the First State National Historical Park visitor center (1 hour) and then tour the historic town of New Castle (2 hours).

Afternoon: Visit the Delaware History Museum and stroll the colonial streets.

Evening: Enjoy a seafood dinner by the Delaware Bay.

Find Hotels

Day 8: Delaware to Connecticut via Scenic Route

Morning: Depart early, taking Route 44 through the Pine Barrens for a quiet drive.

Afternoon: Cross into Connecticut, stopping at the historic Old State House in Hartford (1 hour).

Evening: Arrive in Mystic, check into a waterfront inn, and wander the historic downtown.

Find Hotels

Day 9: Connecticut Coastal History

Morning: Tour the Mystic Seaport Museum (2 hours) and learn about early American maritime life.

Afternoon: Drive to New Haven to see the New Haven Green and historic Yale campus exterior (1.5 hours).

Evening: Return to Mystic for dinner at a historic tavern.

Find Hotels

Day 10: Connecticut to Plymouth, Massachusetts

Morning: Travel north on Route 1A, enjoying coastal vistas and small New England towns.

Afternoon: Arrive at Plymouth Rock and the Plymouth Pilgrim Memorial (2 hours).

Evening: Stay at a historic inn in Plymouth and dine on local clam chowder.

Find Hotels

Day 11: Plymouth to Salem, Massachusetts

Morning: Visit the Mayflower II and the Pilgrim Hall Museum (1.5 hours).

Afternoon: Drive to Salem via scenic Route 3; explore the Salem Witch Museum and historic houses (3 hours).

Evening: Enjoy a ghost‑tour walk through Salem’s historic streets.

Find Hotels

Day 12: Salem Historic Exploration

Morning: Tour the House of the Seven Gables and the Peabody Essex Museum (2 hours).

Afternoon: Stroll the historic waterfront and visit the Old Burying Point Cemetery (1 hour).

Evening: Dine at a colonial‑style restaurant and stay overnight in Salem.

Find Hotels

Day 13: Boston – Freedom Trail

Morning: Begin the Freedom Trail at Boston Common, visiting the Massachusetts State House (2 hours).

Afternoon: Continue along the Trail to the Old North Church, Paul Revere House, and Faneuil Hall (3 hours).

Evening: Enjoy dinner in the historic North End and stay at a boutique hotel.

Find Hotels

Day 14: Boston to Ben & Jerry’s Headquarters, Waterbury, Vermont

Morning: Depart Boston on Route 2, enjoying the Green Mountain scenery.

Afternoon: Arrive at the Ben & Jerry’s Factory for a guided tour and tasting (2 hours).

Evening: Overnight in a charming Vermont inn with farm‑to‑table dinner.

Find Hotels

Day 15: Vermont Exploration & Return Toward D.C.

Morning: Visit the nearby Shelburne Museum (2 hours) and explore local artisanal shops.

Afternoon: Begin the scenic drive back south via Route 7, stopping at historic towns in New Hampshire.

Evening: Stay overnight in a historic inn in the White Mountains region.

Find Hotels

Day 16: White Mountains to Washington, D.C.

Morning: Enjoy a short hike on the Mount Washington Auto Road (1.5 hours).

Afternoon: Continue the southbound journey on backroads, crossing into Pennsylvania’s historic towns.

Evening: Arrive back in Washington, D.C., and relax at your hotel.

Find Hotels

Day 17: Leisure Day in Washington, D.C.

Morning: Revisit any favorite museums or explore the U.S. Capitol Grounds (2 hours).

Afternoon: Stroll through historic Georgetown and shop for souvenirs.

Evening: Celebrate the trip’s conclusion with a dinner cruise on the Potomac River.

Find Hotels

Day 18: Departure

Morning: Pack and enjoy a final brunch at a historic café.

Afternoon: Return the rental car and fly out of Dulles Airport back to Knoxville.

Evening: Arrive home with memories of an unforgettable historic road‑trip.

Find Hotels

Time and Cost Estimates

  • National Archives – 2 hrs – $0 (free)
  • National Museum of American History – 1.5 hrs – $0 (free)
  • National Air and Space Museum – 2 hrs – $0 (free)
  • International Spy Museum – 2 hrs – $25
  • National Postal Museum – 1.5 hrs – $0 (free)
  • Udvar‑Hazy Center – 2 hrs – $0 (free, parking $15)
  • Gettysburg National Military Park – 3 hrs – $20
  • Gettysburg Museum & Visitor Center – 1.5 hrs – $15
  • Amish Heritage Center – 2 hrs – $10
  • First State National Historical Park – 3 hrs – $0 (free)
  • Delaware History Museum – 1 hr – $8
  • Old State House, Hartford – 1 hr – $10
  • Mystic Seaport Museum – 2 hrs – $28
  • Plymouth Rock & Pilgrim Memorial – 2 hrs – $0 (free)
  • Mayflower II – 1.5 hrs – $20
  • Salem Witch Museum – 1 hr – $12
  • House of the Seven Gables – 1.5 hrs – $15
  • Peabody Essex Museum – 2 hrs – $30
  • Freedom Trail (guided) – 5 hrs – $35
  • Ben & Jerry’s Factory Tour – 2 hrs – $15
  • Shelburne Museum – 2 hrs – $18
  • Mount Washington Auto Road – 1.5 hrs – $45
  • Parking & Fuel (overall) – — – $350
  • Total Estimated Cost – — – $819

Tips

If you need to shorten the trip, consider dropping the Vermont leg and allocating the extra day to additional time in Washington, D.C., or Boston. To extend the journey, add a day each in Connecticut’s coastal towns, explore the historic Hudson Valley in New York, or spend extra time in the White Mountains for hiking and scenic drives. All routes favor scenic byways and avoid interstates, ensuring a leisurely pace and plenty of historic charm.

0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version