2026 marks a milestone: America’s 250th birthday. It’s the perfect excuse to explore the places, stories, and experiences that shaped our country. As a self-proclaimed history buff, I am excited to kick off this monumental celebration. And whether you’re drawn to historic cities, scenic drives, or small towns brimming with local flavor, this anniversary offers a chance to plan a meaningful journey that goes beyond the usual tourist stops. However, planning the ideal itinerary or thinking about it can be daunting. Here is a quick list of tips that will help you plan your America’s 250th road trip.
Plan Early, Pick Your Regions & Know Your Crowd
The big anniversary means cities and regions across the U.S. are planning special events. From Boston to Philadelphia to Washington, D.C., and all across the fruited plains, there is no shortage of opportunity to step into history.
Likewise, smaller towns, historic battlefields, and national parks are joining the festivities, so think about what draws you most and the style of commemorations that suit you and your travel buddies best– history, food and drink, family-friendly activities, or scenic drives– and map out a region to focus on.
Check Event Calendars and Official Resources
Before you go, dive into official America250 websites, state tourism boards, and local calendars. These will list events, tickets, and seasonal programming you won’t want to miss. By tapping into a variety of resources, you’ll be able to make the most of your time and experience.
It’s also a good idea to think hyper-local and venue-specific. Many smaller towns and attractions are putting together outstanding celebrations and events. You might even discover exclusive discounts and savings associated with the 250th.
If you are interested in one of the larger celebrations or busier attractions, it’s prudent to begin your plans as soon as possible (like today). Afterall, the semiquincentennial is certain to be a busier time than usual. And keep in mind, even if your focus is on major celebrations, it’s still possible to spot Pull Over moments along the way, such as a local café, a historic tavern, or a small vineyard that captures the spirit of the region.
Timing and Crowds
High-profile events such as July 4th in Boston, New York, or Washington, D.C., will draw thousands of visitors. Again, if crowds aren’t your thing, consider smaller, more intimate celebrations. One of my favorite July 4th events was at Patrick Henry’s Red Hill in Brookneal, Virginia. History paired with an impressive fireworks display made for a memorable celebration. I’m sure they’re gearing up for an extra special celebration in 2026.
Speaking of crowds, if you have flexibility and want to experience some of the popular historic attractions, consider visiting on weekdays or after peak dates.
My advice: pick a few key stops and give yourself the time to explore them slowly. For example, instead of rushing through Washington, D.C., you might spend a day on the National Mall and another exploring the lesser-known historic neighborhoods nearby. It’s about capturing the experience, not just checking sites off a list.
“Planning your America 250 trip? Start with the official national sites, like America250.org and the White House’s America 250 page, to see calendars, events, and highlights. Then check your state’s semiquincentennial commission—many have programs to make exploring historic sites even more fun, like Virginia’s America250 Passport. These resources are perfect for getting you started on your America’s 250th Roadtrip!”
Anna Marie
Travel Logistics for Planning Your America 250 Road Trip
Driving is often the easiest way to combine major destinations with hidden gems, but again, early booking is essential.
Hotels and inns near popular sites and events will fill fast. I suggest booking your accommodations as soon as you know your travel dates. Especially if you’re trying to plan for July 4th– this will be the most challenging time to score decent accommodations at a reasonable price.
If your schedule is flexible, you’ll find better lodging rates and availability after high-demand dates. Even in major cities, a flexible itinerary pays off; you can take a scenic detour, stop at a museum or gallery, or explore a storied tavern along the way. Think of it as a road trip with history as your guide.
It’s also a good idea to research other attractions nearby if you are traveling to a specific destination. For example, James Monroe’s home, Highland, is only a couple of miles away from Thomas Jefferson’s Monticello, and both can be seen easily in a day. You will maximize your time and historic visits by building an itinerary that makes navigating simple and sensible.
If historic taverns appeal to you, here is the link to a classic post I wrote detailing several taverns with colonial roots. 2026 is the ideal time to mark America’s historic milestone with a traditional meal served as it would have been all those years ago.
Incorporate Local Flavor
As previously mentioned, some of the best America 250 trips mix well-known landmarks with smaller, equally historic stops. Think beyond the big cities. From George Washington’s Mount Vernon and his birthplace at Pope’s Creek, Virginia, to his boyhood home at Ferry Farm, you can also explore pivotal battlefields like Yorktown, Guilford Courthouse, and King Mountain. Branch out even further to places like Mount Rushmore, the national parks, and the myriad scenic byways that are all part of the 250th celebrations. Planning a route that blends iconic sites with off-the-beaten-path gems makes your trip richer, more memorable, and full of discoveries you won’t find on a standard itinerary.
America 250 Road Trip Ideas to Get You Started
If you’re not sure where or how to begin planning an America 250 road trip, you don’t have to reinvent the wheel. Get it? Several national initiatives tied to the 250th anniversary can help spark ideas and give your itinerary some structure. Think of these as starting points you can adapt to your own travel style.
America 250–inspired road trip routes are highlighting historic sites, scenic drives, and cultural stops across the country.
The Great American Road Trip concept encourages coast-to-coast travel, connecting landmarks, national parks, and classic Americana along the way.
Historically themed routes, such as retracing the Washington-Rochambeau Revolutionary Route to Yorktown, offer a built-in story to follow.
National parks and iconic landmarks, from Mount Rushmore to parks out West, will also be part of the broader celebration.
Wrap-up Tips
If you haven’t begun planning your America 250th road trip or celebration, don’t worry—it’s not too late. Planning ahead can help with accommodations, but having experienced America’s bicentennial as a kid, I encourage you to find some way to mark this once-in-a-generation milestone.
I can sincerely say that one of my fondest childhood memories is of the Spirit of ’76, the excitement, and enjoyment of the celebrations surrounding the bicentennial. America had just wrapped up a terrible war in Vietnam and was overdue to have cause for joy and reverie. The bicentennial provided just such an event. America threw a birthday party, and it was memorable.
Start planning early, choose your regions thoughtfully, and build an itinerary that balances history, local flavor, and scenic stops. Keep it flexible because sometimes the best experiences are the ones you stumble upon when you say, Pull Over and Let Me Out.
And if you’re ready to start jotting down ideas, consider keeping a simple checklist: major anniversary events, historic sites, small towns to explore, and unique Pull Over moments along the way. Your 250th road trip doesn’t have to be perfect—it just has to be memorable.
You can mark America’s 250th with the Pull Over and Let Me Out 2026 Book Club– join us as we travel back to America’s founding through literature! Also, tune into the Pull Over and Let Me Out Podcast, where I feature several interviews pertaining to America 250!
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