Hollyday Planner

See the itinerary for a quick summary

10 states! 1 epic road trip. We started with a flight to DC then saw everything we could. Our daughter says we didn’t miss any historical blade of grass. lol. This is one of my road trips I get asked most often to share. We packed a lot into 9 days. It would be easy to split much of this up into shorter trips & see more things in one area. I included notes for things we didn’t do to help give inspiration for your trip.

Day 1

• Ford’s Theater – Tickets are required. We didn’t visit The Petersen House (where President Lincoln died). There was a very long line even early in the morning. But it’s just across the street.
• National Archives Museum – Go see our original US Constitution and other founding documents. Free, but required reservation. It’s a quick stop. They have a nice museum with lots of other great history. No pictures allowed (so none in this post).
• Smithsonian Museum of Natural History: Don’t miss the Hope Diamond. All of the Smithsonian’s are free. Just walk in. Most have a cafe.
• Smithsonian Museum of American History: A wide variety of American history. The original Star-Spangled banner, Dorothy’s ruby slippers and so much more.
• Library of Congress – Fun to walk into and see.
• Smithsonian Museum of Air & Space – My personal favorite. It was closed when we were there but they had moved most things out to their annex. We get there later in our trip.
• Things to walk around & see – DC is a great place to walk around & take in the sites. For anything you’d want a tour, check individual websites for rules. We just wanted to see the buildings on this trip. I’d been before and been in most of the buildings. My family wasn’t interested in going in. We split these up over two days.
  • Supreme Court
  • US Capital
  • White House
  • WWII Memorial
  • Vietnam Veterans Memorial
  • Lincoln Memorial
  • Korean War Memorial
  • Martin Luther King, Jr Memorial
  • FDR Memorial
  • Jefferson Memorial

Day 2

• Bit of a heavy start to the day, but highly recommend.
• Arlington National Cemetery – Free entry. We took the subway out there. Once in, they have a hop-on-hop-off system for getting around. Some of the more popular stops.
  • Welcome Center
  • Changing of the Guard
  • JFK Grave
  • Arlington House – do go inside. Check with ticket requirements.
  • General Pershing’s Grave – highest ranking officer in Arlington
• Pentagon – close by Arlington.
• US Holocaust Memorial Museum – Reservations are required and they can be hard to get. This is a heavy museum but highly recommend. I still have strong memories of going as a younger kid. Be sure to check early & often for reservations.
• National Mall – Fun to grab a picnic lunch from one of the food trucks.
• Washington Monument – I’ve never gone to the top.
• National Cathedral – It was closed for remodeling when we were there, but I love this building.
• Walk down Embassy Row – It’s a long walk. But, so fun to see all the very different buildings for each country.
• Washington Harbor – Great place to stop & sit to grab some dinner. Also, Watergate Hotel is within view.
• Georgetown
• Lafayette Square
• Some options for evening activities (if buildings & monuments have become too much):
  • JFK Center for performing arts
  • Ford’s Theater
  • National Theater

Day 3

• Time to pick-up the car rental and start the road trip!
• Steven F. Udvar-Hazy Center With the Air & Space museum closed they had moved things to this building. This is the normal Annex building for the museum. I would recommend going even when the museum is open. There are great things to see.
• Antietam National Battlefield (Maryland). Great history. There is an observation tower. It’s not from the period, but still old. Be sure to walk to the top to see the views.
• Gettysburg National Military Park (Pennsylvania) – MASSIVE! You’ll do the driving tour around the full park. We stopped at a good number of the memorials. For the Gettysburg Address, they don’t actually know where President Lincoln stood. Because at the time, the speech was considered bad. After seeing the battlefield, I recommend going downtown for lunch. It’s a super cute downtown.
• Fort Marcy – This was obviously a special stop for us
• Back to DC to drive around and see the monuments lit up at night

Day 4

• Baltimore (Maryland)
  • Fort McHenry – Where Francis Scott Key wrote the Star-Spangled Banner.
  • Edgar Allen Poe House & Museum – we skipped this but it was on my wish list
  • Star Spangled Banner Flag House – closed the day we were here
• Brandywine Creek State Park – Wilmington (Delaware). It was tough finding things in Delaware. We took a little walk through this park. It was very pretty.
• Longwood Gardens (Pennsylvania) – Wow. This was more popular than we were expecting. But the site is really beautiful. We don’t do a lot of gardens, but really glad we did this one. Tickets required.
• Valley Forge (Pennsylvania) – They do have replicas of the huts used at the time. But the highlight for us was General Washington’s Headquarters. It’s still the original.
• Hotel in Philadelphia

Day 5

• Philadelphia
  • Independence Hall – Where the Declaration of Independence was signed. I didn’t know advanced reservations were required. So we didn’t get to go in on this trip. Be sure to check the site for current requirements. Requires advanced reservation.
  • Liberty Bell – Got to see this though!
  • Ben Franklin Museum – Really enjoyed this museum.
  • Rocky Steps & Statue at the Philadelphia Museum of Art – We didn’t stop for the photo Op, but wanted to call out it’s there.
• Washington Crossing Historic Site (Pennsylvania / New Jersey border) – Site where General Washington crossed the Delaware River. We enjoyed this area. There are a few different interesting things in the area.
• Morristown National Historical Park – Sadly closed when we were there.
• Thomas Edison National Historical Park (New Jersey)
• New Haven (Connecticut)
  • Yale University – We enjoyed walking around the beautiful campus. Be sure to check out the famous Skull & Bones.
  • Amistad Memorial
  • Long Wharf

Day 6

• Newport (Rhode Island) – a new personal favorite. I’ll have a few other recommendations from a later girls’ trip back to this area.
  • Cliff Walk – This is a long walking path along the coast line. We walked a section of it starting at the beach. Once we got up to the mansions we also walked a portion of it there.
  • Newport Mansions – There are a few of these available. I haven’t picked a favorite yet. The Breakers is probably the most popular. It’s a Vanderbilt mansion. I recommend getting a pass to see as many as you have time to.
  • Bowen’s Wharf – This is a great place to take a break. Grab something to eat & shop
  • Ocean Drive – Fun drive around the coast.
• Plymouth Rock (Massachusetts) – It’s really just a quick photo Op. There is a replica boat nearby but we just wanted to see the spot where the pilgrims landed.
• Boston (Massachusetts) – This is where we got a hotel for the remainder of the trip. From here, it’s easy to take day trips.
  • The Barking Crab – Great spot for dinner in Boston Harbor
  • Longfellow House – We drove by to see it.
  • Harvard / MIT – On a future trip I talk more about the Harvard Art Museum. We didn’t see it on this trip, but I need to call it out. It was incredible. On this trip, we just wanted to see the two campuses.
• Hotel: Boston
• PRO TIP: Driving in Boston is difficult at best. Our hotel was close to the airport. To just get around town, I recommend using the subway.

Day 7

• Boston Tea Party Recreation– I only recommend this if there are young kids. Tickets required.
• Bell in Hand Tavern – Highly recommend. Great restaurant & very old. It’s been a long-time favorite of mine and anybody I’ve been with enjoys it.
• USS Constitution – I love the USS Constitution. “Old Ironsides”. So fun to go aboard and explore. There is also a modern ship that was included in the tour. Ticket rules seem to change every time I’ve been. Be sure to read ahead.
• Freedom Trail – These are mostly grouped together and generally walkable. However, they have early hours. So it’s hard to get them all in one day. Some are separate tickets. Some can be grouped together.
  • Old North Church – add the Crypt tour
  • Paul Revere’s House – loved this
  • Faneuil Hall – Marketplace downstairs, historial upstairs
  • Old State House & Boston Massacre site – The site is a plaque in the sidewalk in front of the Old State House. The building itself has some great history inside.
  • Granary Burying Ground – The more famous of the cemeteries on this list.
  • Boston common – the large park
  • Old South Meeting Hall
  • Massachusetts State House – the current state capital. We didn’t tour.
  • Park Street Church
  • King’s Chapel & King’s Chapel Burying Ground
  • Boston Latin School / Benjamin Franklin Statue
  • Old Corner Bookstore – The building structure is historical, but nothing inside was preserved. It was a Chipotle last time I was in Boston.
  • Copp’s Hill Burying Ground – Closer to Paul Revere’s House.
  • Bunker Hill Monument – out by the USS Constitution.
• Cheers Bar – After walking down Boston Common you’ll be close.
• Other things in the area we didn’t do on this trip:
  • Red Sox Game or tour Fenway Park
  • John Adam’s House

Day 8

• Salem (Massachusetts)
  • The House of the Seven Gables – And birthplace of Nathaniel Hawthorne. You get to explore all through the house. Nathaniel was raised right next door to the house that gave him the inspiration for his book. Tickets required.
  • Salem Witch Museum – I only put this one here to warn don’t go. It’s a wax figurines with a voice over detailing the history of the witch trials. Then a small exhibit of the history of witches in pop culture. They did have one beam original to the building where the trials took place is all. It’s a tourist trap.
  • Rockafellas – Great restaurant!
  • Downtown Salem – super cute downtown. I really liked Salem.
  • Old Burying Point / Salem Witch Memorial – Charter Street Cemetery. The memorial is on the walk in. But there are some notable graves. Including a Mayflower Pilgrim.
  • The Witch House – Home of the judge of the witch trials. This I highly recommend. Great view of life in the times. Plus the only real connection from the era still available.
• Portland (Maine)
  • Portland Head Light House – Exactly what you think of when you imagine a lighthouse.
  • Portland Observatory – we didn’t go in, but wanted to see it.
  • Wadsworth-Longfellow House – again, didn’t go in but wanted to see it.
  • DiMillo’s on the Water – If you also want Maine lobster while in Maine. A boat converted into a restaurant permanently docked. It’s a staple of Portland.
  • Back to Boston for the night

Some other things around the area we skipped:

• Harbor Trail & Historic houses  
• Strawbery Banke Museum
• USS Albacore Museum
• Prescott Park
• (ME) Old York
  • Historical Society
  • Gaol (prison)
• Portland’s Old Port
• Tate house
• Victoria Mansion
• Ferry to Peaks Island
• Duckfat Friteshack
• Lincoln (speakeasy)

Day 9

• Minute Man National Historical Park – site of the firsts shots of the Revolutionary War.
• America’s Stonehenge (New Hampshire) – Fun & interesting place to visit.
• Lost River Gorge & Boulder Caves (New Hampshire) – Highlight of the trip. This is when I first got asked how I find these places. Just beautiful. And the trail was super easy. Nice wooden walkway. Tickets required.
• Ben & Jerry’s Factory (Vermont) – The tour was closed, but we loved the ice cream. And flavor graveyard.
• Morse Farm Maple Sugarworks Farm (Vermont) – Learn all about maple syrup. Adorable farm & delicious maple treats.
• Return to Boston

Some other things in the area:

• Billings Farm & Museum
• Marsh-Billings-Rockefeller National Historical Park