【Travel] Planning - 10‑DAY EAST COAST HISTORY ROAD TRIP

 

Boston → Plymouth → Newport → Long Island → NYC → Philadelphia → D.C. → Antietam → Gettysburg → Richmond → Williamsburg/Jamestown/Yorktown

🗓️ DAY‑BY‑DAY ITINERARY

Day 1 — Boston (Revolutionary America)

Themes: Revolution, early resistance Highlights:

• Freedom Trail (16 sites)

• Old North Church

• Boston Tea Party Ships & Museum

• Faneuil Hall

Overnight: Boston

Day 2 — Plymouth → Newport

Themes: Early settlement, Pilgrims, Wampanoag history

• Plimoth Patuxet Museums

• Plymouth Rock Drive to Newport, RI (1.5 hrs)

• Explore colonial Old Quarter

• Optional: Gilded Age mansions (contextual contrast)

Overnight: Newport

Day 3 — Ferry to Long Island (1 night stay)

Themes: Coastal colonial settlements, early maritime history Drive to New London, CT → take ferry to Orient Point, Long Island Explore:

• Historic Greenport village

• Shelter Island (optional)

• Sag Harbor Whaling & Historical Museum (excellent settlement-era context)

Overnight: Long Island (Greenport or Sag Harbor)

Day 4 — Long Island → New York City

Drive to NYC (2–2.5 hrs depending on location) Themes: Immigration, early republic, modern identity

• Ellis Island Immigration Museum

• Statue of Liberty

• Federal Hall (Washington’s inauguration site)

Overnight: NYC

Day 5 — Philadelphia (Birth of the Nation)

Drive NYC → Philadelphia (2 hrs) Themes: Revolution, Constitution, early government

• Independence Hall

• Liberty Bell

• Museum of the American Revolution

• Betsy Ross House (optional)

Overnight: Philadelphia

Day 6 — Baltimore → Washington, D.C.

Drive Philadelphia → Baltimore (1.5 hrs) Themes: War of 1812, early national identity

• Fort McHenry

Continue to Washington, D.C. (1 hr) Themes: Founding ideals → national memory

• National Mall monuments

• National Archives (Declaration, Constitution)

Overnight: Washington, D.C.

Day 7 — Antietam → Harper’s Ferry

Drive D.C. → Antietam (1.5 hrs) Themes: Civil War turning points

• Antietam National Battlefield (bloodiest single day)

Drive to Harper’s Ferry (30 min) Themes: Abolition, John Brown’s Raid

• Historic Lower Town

• Confluence of Potomac & Shenandoah

Overnight: Harper’s Ferry or Gettysburg

Day 8 — Gettysburg (Full Civil War immersion)

Drive to Gettysburg (1 hr) Themes: High-water mark of the Confederacy

• Gettysburg National Military Park

• Auto tour or ranger-led program

• Eisenhower National Historic Site (optional)

Overnight: Gettysburg

Day 9 — Richmond (Civil War Capital)

Drive Gettysburg → Richmond (3.5 hrs) Themes: Confederate capital, industrial war

• American Civil War Museum (Tredegar Iron Works)

• Richmond National Battlefield

• Confederate White House (contextual, not celebratory)

Overnight: Richmond

Day 10 — Jamestown → Williamsburg → Yorktown (Colonial Triangle)

Drive Richmond → Jamestown (1 hr) Themes: Settlement, Indigenous encounters

• Jamestown Settlement

• Historic Jamestowne (archaeology site)

Drive to Williamsburg (20 min) Themes: Colonial life, pre‑Revolution society

• Colonial Williamsburg

Drive to Yorktown (20 min) Themes: Revolutionary War finale

• Yorktown Battlefield (Cornwallis’ surrender)

Overnight: Williamsburg or Richmond END OF TRIP IN VIRGINIA

🧭 Why this 10‑day route works beautifully

• It follows the chronological arc of American history from settlement → revolution → civil war.

• Long Island fits naturally between Newport and NYC without detours.

• Ending in Virginia lets you close the journey at the birthplace of English America and the final battlefield of the Revolution.

• Driving segments are reasonable (no 7‑hour slogs).

• Each day has a clear historical theme, perfect for your educational storytelling style.