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The Ultimate East Coast Political History Road Trip

With the 2016 presidential election (mercifully) just days away, the volatile nature of this year’s contest has made the topic of politics a fixture in our day-to-day lives. On the FlipKey blog we want to forget all about the “who do you support” or “I’m moving to Canada” rhetoric and focus more on the incredible political history of America’s east coast. From presidential libraries and homes, to famous speeches and scandals, we’ve chosen seven spots along the east coast to make for an educational road trip.

JFK Library and Museum in Boston, Massachusetts

JFK Library and Museum in Boston, Massachusetts

Boston, MA – John F. Kennedy Presidential Library & Museum 

Your journey starts at the gorgeous JFK Presidential Library in Boston designed by famed architect I.M. Pei. In a city full of historic sites, the JFK Library is a wealth of information on his too-short life. The 35th President of the United States was born and raised in Massachusetts, and the 10-acre grounds include trees, shrubs, and roses reminiscent of Cape Cod.

The interior of the museum portrays the life, leadership, and legacy of President Kennedy. Exhibits include a look at the famous 1960 presidential campaign, a tribute to his younger brother Robert, and a collection of historical materials chronicling mid-20th century politics and life.

Shop in the museum store or dine in the JFK Café. Visitors can walk along the Boston Harborwalk or picnic on the grounds. From May to October, President Kennedy’s 26-foot sailboat Victura is on display. Tickets cost $14 for adults, and children under 12 get in free.

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Oyster Bay, NY – Sagamore Hill 

Drive past Brooklyn and Queens and head out to Oyster Bay, NY to visit Sagamore Hill, the home of one of America’s manliest men, Teddy Roosevelt. Teddy lived here from 1885 until his death in 1919.

Teddy Roosevelt bought 155 acres on Long Island in 1880, and hired architects to build the home at his wife’s direction. She helped plan the house, with its many rooms, wide verandahs, and sweeping views of Long Island Sound, but did not live to enjoy it. Teddy raised six children in the home with his second wife, Edith.

During Roosevelt’s time in office, his “Summer White House” was the focus of international attention. It was the political and personal home for Teddy and his whole family. In 1900, Republican leaders gathered at the house to hear Roosevelt accept his nomination for vice president as William McKinley’s running mate. It became his unofficial campaign headquarters in 1904 and in 1912. On the day before he died there, on January 6, 1919, Roosevelt asked Edith, “I wonder if you will ever know how I love Sagamore Hill.”


Explore the natural surroundings and be inspired by the legacy of one of America’s most popular presidents. The home is open to the public by guided tour. Almost all the furnishings are original. Also on the site is the Theodore Roosevelt Museum, which chronicles the life and career of the President.

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Philadelphia, PA – Independence Hall

Independence Hall in Philadelphia, Pennsylvania

Independence Hall in Philadelphia, Pennsylvania

Men like George Washington, Benjamin Franklin, and Thomas Jefferson planted the first seeds of Democracy at Independence Hall. Independence Hall is the location of the signing of the Declaration of Independence in July of 1776when the founding fathers said “Enough is enough” to Great Britain. The first American flag was flown here one year later, and the US Constitution was drafted in this building 10 short years after that. The original liberty bell was housed here, but has since been moved to another pavilion.

Independence Hall was restored several times, changing the appearance of the building. In 1950 the National Park Service restored it back to its 1776 appearance. Sadly, most of the furniture inside Independence Hall is not authentic—in 1778, British troops occupied the building and used the furniture as firewood!

Independence Hall is located in the middle of the 45-acre Independence National Historical Park. The historic building can be visited free of charge by guided tour between March 1 and December 31. It is open late in the summer, and visitors can take the opportunity to explore on their own.

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Gettysburg, PA – Gettysburg Battlefield

battlefield cannon (Gettysburg, Pennsylvania).

This small town in Pennsylvania was thrust into the spotlight during the bloodiest battle in American history between the Union and Confederate troops during the American Civil War. Over three horrible days in July 1863, over 50,000 soldiers died on these hallowed grounds. In November of that same year, President Lincoln wrote and delivered the famous Gettysburg Address during the commemoration of the battle.

Today, this 6,000-acre Civil War military park, dedicated to soldiers who fought here, is a beautiful and somber place. There are a number of group tours offered by different carriers—some are on horseback, others on Segways, more by bus or from the comfort of your own car with an audio tape or iPad app. Of course, the best way is to tour the area is with a knowledgeable Park Ranger. Licensed Battlefield Guides train for years and must pass extensive tests administered by the National Park Service to qualify to give tours.

You’ll want to start at the Visitor Center when you arrive and use this building as your home base. Grab an itinerary to see the offerings of the day and week. The Visitor Center also serves as a museum and shows educational movies. There are other special historic sites that are part of the Gettysburg National Military Park, including the Soldiers’ National Cemetery, the George Spangler Farm, the Eisenhower National Historic Site, the David Wills House and the Rupp House.

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Washington DC – Ford’s Theater

Ford's Theatre, Washington DC

Ford’s Theatre, Washington DC

From what is arguably Lincoln’s greatest moment to his worst—make your next stop further south at Ford’s Theater in Washington DC, the site of his assassination in 1865 by John Wilkes Booth. The President was carried across the street to Petersen’s boarding house where he remained unconscious through the night, and died the next day.

Today, Ford’s is a working theatre, historical monument, world-class museum and learning center celebrating the life and legacy of Abraham Lincoln. On the top level, the restored and renovated theater produces plays and musicals exploring the American experience and Lincoln’s legacy.

Located below the theater is the museum, which transports visitors to 19th-century Washington. The theatre, museum and education center educate patrons about Civil War Washington and Lincoln’s life, assassination and legacy. Highlights of a Ford’s Theatre visit include presentations by actors and National Park Service rangers, exhibits exploring Lincoln’s presidency and the Civil War, and a 34-foot tower of Lincoln books. The collection also includes artifacts related to the assassination, such as Lincoln’s overcoat, Booth’s derringer, Major Rathbone’s gloves and the contents of Lincoln’s pockets when he was killed.

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Charlottesville, VA – Monticello

Monticello - Charlottesville, VA

Monticello – Charlottesville, VA

Just over three hours south of DC you’ll find Charlottesville, Virginia. Monticello was designed by Thomas Jefferson in the late 1700s to be a home, plantation, and farm. It’s known as his “essay in architecture”. Jefferson (third president and author of the Declaration of Independence) worked on Monticello, one of America’s most famous houses, for over four decades, updating and enlarging the home based on his tastes. There are Roman, French, and other architectural influences blended throughout the home. Monticello is full of Jefferson mementos and the versatile structure is a testament to this early Renaissance man.

Outside, on the grounds, Jefferson continued his work, showcasing his knowledge of gardening and landscaping. Both ornamental and vegetable gardens, as well as two orchards, a vineyard, and an 18-acre grove were included in his landscape plans.

The Thomas Jefferson Foundation, a nonprofit organization, purchased the property in 1923 and continues to operate it as a museum and educational institution. Tours of the house and gardens are available March to October. House tours are offered daily, though there is a fee for admission.

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Palm Beach, FL – Butterfly Ballot

Poll Worker Assists Sr. Voter

After a long but fulfilling road trip, treat yourself to a final stop in Palm Beach, Florida, one of the counties where the Butterfly Ballot almost ruined the 2000 presidential election. Many voters cast their vote for the opposition, either Al Gore or George Bush, by mistake!

Voting issues were rampant in the state of Florida: some electronic ballots malfunctioned, lawsuits were brought over the butterfly ballot, and who can forget the notorious “hanging chad”?

You can relax in Palm Beach for the last few days of your road trip by walking along Lake Trail or chartering a boat for a deep sea fishing adventure.

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There are hundreds more attractions for political history enthusiasts along the east coast. We’ve left off some major ones like the White House, Capitol Building and Lincoln Memorial—and that’s just in Washington DC! If this election has ignited your love for politics and travel, we encourage you to plan your own road trip and get moving. Staying in vacation rentals along the way will save you a lot of money, plus you’ll have the space, privacy, and amenities you’re used to at home.