The Ultimate Dallas to Boston Road Trip Itinerary For 2023

This post may contain affiliate links. We may receive a small commission, at no cost to you, if you make a purchase. Read Disclosure.

A Dallas to Boston road trip offers an experience like no other. Not only does the journey cover over 1,500 miles, passing through several states, each with its own distinctive culture, history, and natural beauty, but you also get to drive along the iconic Route 66.

As you drive, you’ll see some of America’s most iconic landmarks such as the Grand Canyon, Chicago, Niagara Falls, and New York City.

Taking a road trip from Dallas to Boston allows you to experience the freedom and adventure of traveling at your own pace, discovering hidden gems and meeting friendly locals.

For those seeking an unforgettable travel experience and are thirsty for adventure, keep reading to see what are the best stops to take on this incredible adventure.

But first…

How Long Do You Need to Road Trip From Dallas to Boston?

The amount of time you should spend on a Dallas to Boston road trip depends on your travel style and preferences.

The journey can be completed in about 26 hours of non-stop driving (1,761 km), but it’s recommended to take at least two weeks to enjoy the sights and attractions along the way.

When we did our Dallas to Boston road trip, we went with my parents who wanted to come visit us from Australia after we moved to Raleigh, North Carolina.

They had four weeks set aside, so we decided to put a cool road trip experience together for them, incorporating places I knew they’d love and crafting it around their flight into Dallas.

They were arriving in May so we knew the South east region would be great weather wise and have less crowds.

We were also driving to Minnesota before hand for a work campaign, so decided to drive down from there to pick them up and then come back to Raleigh after Boston.

This is a road trip adventure is one you could do with any length of time, but I felt four weeks was just about the right time. It allowed us to go at our own pace, incorporate a few down days where we can recover from long stints on the highway, and maximise our time at each place.

In the following Boston to Dallas road trip, you can adjust the itinerary and number of days at each place as you see fit.

If you have more time, I will recommend some other highlights you can consider that we didn’t do on this trip, but have on other times.

You could even do it in as little as two weeks – Americans love those kind of fast paced vacations.

You decide.

Rather than adding in time frames into this itinerary, I’ll cover the route and activities and offer suggested time to spend in each region. That will make it easier for you to adjust.

At A Glance: Dallas to Boston Road Trip

For this road trip, we planned the itinerary around history and cultural experiences, including things my parents love, like music, movies, and war history.

I recommend you plan your travels around a theme or your passions and interests as there is so much to see and do in this region.

For example if you want beaches and theme parks, you can add in some side trips to the Gulf Shores in Alabama and Orlando.

There are so many options, and while driving times in the US can be pretty long (plan accordingly) you can “easily” detour to these places.

This road trip itinerary incorporates what we think are some of the best US cultural and historical experiences with some natural beauty thrown in!

Map of this Dallas to Boston Road Trip

To help you plan routes, travel time, and schedule, here is a map of this Dallas to Boston road trip…

If You’re Starting in Minnesota…

We started the first ten days of our Dallas to Boston road trip in Minnesota.

If you have more time on your side, I recommend starting your trip driving to Bloomington, Minnesota and exploring the Mall of America and a few other cool things to do there.

Take a visit to Paisley Park – Prince’s home and a stay at the Great Wolf Lodge – their favorite family resorts in the US.

Our US road trip adventure really went for six weeks, but the part from Dallas to Boston was four weeks.

Save Money on Sightseeing on this Dallas to Boston Road Trip

If you’re traveling to multiple cities included in this road trip itinerary over a 30 day period, we recommend you get the USA Sightseeing Pass.

This allows you to choose from over 300 attractions in 12 USA destinations saving you up to 70% on attraction fees.

Many of the cities/regions listed here are included in the sightseeing pass.

The Ultimate Dallas to Boston Road Trip

Now you have the finer details covered, it’s time to show you the route for the ultimate road trip from Dallas to Boston. Starting in…

Dallas, Tx

We picked up my parents from the airport in the afternoon ready to start our month road trip the following morning.

We decided not to spend much time in Dallas as we wanted to do other things more.

We do recommend you stay here at least for the night to recover from jet lag and so have more energy for the month long fun in store.

I wasn’t planning to do much with our one night stay in Dallas with them as I know how brutal that flight from Australia can be and knew they’d be tired.

But we discovered the JFK Museum was just around the corner from our hotel at the Hyatt Regency.

As they are big JFK fans and have long had conspiracy style discussions over his death, we paid a quick visit (as it was closing time). I wish we had longer as we all really loved it.

Some other popular things to do in Dallas are:

1. Visit the Sixth Floor Museum at Dealey Plaza, which explores the life and legacy of President John F. Kennedy.
2. Explore the Dallas Arboretum and Botanical Garden, featuring 66 acres of stunning gardens and walking trails.
3. Experience the cowboy culture at the Fort Worth Stockyards, which offers rodeos, live music, and western-themed shops and restaurants.
4. Check out the Dallas Museum of Art, showcasing an extensive collection of art from around the world.
5. Shop and dine in the trendy Bishop Arts District, known for its eclectic boutiques and restaurants.
6. Attend a Dallas Cowboys football game at AT&T Stadium, one of the largest and most impressive sports venues in the world.

Waco, Texas

Fixer Upper was something we watched with my parents back in Australia. We all loved it so of course, had to include a stopover in Waco on our way to San Antonio.

It’s only a two hour drive from Dallas so easy to do, and if you have more time, I recommend staying the night.

We loved Waco and it has so much more to offer than just Magnolia related attractions.

But these were definitely the highlights. Be sure to arrive early so you can beat the breakfast lines for Magnolia Table.

They can be up to 4 hours!!! We only had a 20 minute wait and it was worth it. My Dad said it was the best breakfast he ever had.

Don’t miss the cupcakes at the Silos either – delicious!

Waco Video:

San Antonio, Texas

Visiting San Antonio checked off my Dad’s long life dream to see the Alamo. I think it was one of the first movies I remember watching with him.

San Antonio is a beautiful city with its spectacular river walk and will give you an unique historical and cultural US experience.

We loved our stay at The Emily Morgan Hotel, an historic hotel of America, that overlooks the Alamo and is within walking distance to the river walk. It’s also the official Alamo Hotel so will enhance the experience. It’s also known as one of the most haunted hotels in the USA!!

We loved our tour of the Alamo and enjoying the San Antonio River walk.

I recommend staying for longer if you can as there is so much to do in this region.

We especially love the nearby Texas Hill Country and while Big Bend National Park is about a six hour detour west, if you have more time, it’s a fantastic national park free from crowds and located on the Rio Grande River and Mexican border.

Alamo and San Antonio River Walk Video

New Orleans, Louisiana

I highly recommend you stop over in New Orleans on your way to Memphis. We buzzed through this area, only stopping for a night in the middle of nowhere to break up the long drive.

New Orleans is one of our favorite city and possibly the most unique in the USA. It has the best food in the country, with a unique blend of French, Cajun and English cultures, amazing history, and such a fun attitude. Mardi Gras is a must you are visiting at the right time.

You could then either drive over into Florida, or drive up to Memphis via Jackson, Mississippi, or through Alabama which is a surprisingly good state.

You could pick up our North Carolina to Florida road trip plan to head up North via that way. I absolutely love Tennessee though!

New Orleans Video

Memphis, Tennessee

If you love blues, BBQ and Rock N Roll, you will love a stop in Memphis, Tennessee. We recommend at least two nights exploring all this city has to offer and visiting the top Memphis attractions.

We visited as Mum is a die-hard Elvis fan and has wanted to visit Graceland ever since I can remember.

So it was to Graceland we went, even experiencing the treat of staying overnight at the Graceland hotel. We also enjoyed a visit to Sun Studios and afternoon tea with the Peabody Ducks.

Memphis Video

Nashville, Tennessee

Of course, we had to stop at our favorite city in the US. Nashville is just so much fun! If you love music – any style – this is the place to come. I recommend staying here for at least three days.

We made sure my parents got the full Nashville experience with honky tonk music over lunch on Broadway, a blues session at the Bluebird Cafe, learning more about the history of music at the Country Music Hall of Fame and Museum.

We also visited the Johnny Cash Museum, Patsy Cline Museum, and did a backstage tour of the Ryman Theater, and a tour of Studio B.

And the highlight was taking them to see a show at the Grand Ole Opry, which included a backstage tour!

Nashville Video

Franklin, Tennessee

While in Nashville, you can take an easy day trip to Franklin, TN, a small charming town in the deep south full of history, good boutique shopping, and a vibrant music lifestyle.

Many famous musicians live out this way and nearby Liepers Fork, which we also visited for an evening of open mic at Puckett’s Groceries – an iconic musical experience in the Nashville region.

We also loved our tour of Carnton House, famous for a Civil War battle.

If you have more time…

Tennessee is a fantastic road trip destination. We highly recommend you visit the Great Smoky Mountains National Park while in this area.

You will drive through it to get to the next destination on our list. My parents were more interested in the US cultural travel experiences then national parks.

We recommend at least two nights in the Smokies (and stay in the park if you can!)

If there’s no time on this road trip, make sure to add Tennessee to your next trip.

Biltmore Estate, Asheville NC

I knew my parents would love the opulence of Biltmore Estate, North America’s largest home. We love it so much we take all visiting family and have been three times.

I highly recommend the house and garden tour as well as spending time sampling wines at their winery – the highest selling vineyard in the USA!!

We stayed the night at the Biltmore Inn, which I highly recommend. It really enhanced the experience or us and was my parents’ favorite accommodation on our Dallas to Boston Road trip.

Biltmore is also close to Asheville a popular place to visit in the North Carolina mountains.

Lake Lure, NC

Are you ready for my favorite lake in the US?

Lake Lure is my happy place. There is something special about this serene place in the North Carolina mountains. May is a great time to visit before the summer rush as well – but summer is still great!

In Lake Lure we love to amble: paddleboard and swim in the lake, enjoy a boat tour of the lake learning about the history, visiting Chimney Rock State Park and enjoying ice cream while walking on the board walk.

Dirty Dancing lovers will appreciate this lake – it’s where several scenes in the movie were filmed, including the famous lift scene and each year they have a Dirty Dancing festival.

The most beautiful place to stay on the lake with magnificent views is the Lodge on Lake Lure. We loved it. I recommend two to three nights (or even longer if you want to rest awhile).

Lake Lure Video

Gettysburg, PA

Gettysburg made a good stopping off point on our way up to New York. It was about halfway and worth stopping in for at least one night. We stayed for two and really liked it a lot.

I was impressed by the spirit and energy in the town and we all absolutely loved our driving tour with a knowledgeable guide of the Gettysburg Battlefield area. I never expected to like it as much as I did.

It also has a growing food and craft beer scene and ghost tours I want to come back and do as it’s meant to be the most haunted place in the USA.

If you want to be closer to the restaurants and attractions in Downtown Gettysburg, then we recommend staying at the historic Gettysburg Hotel.

If you have more time

You could drive through the scenic Blue Ridge Parkway on the way to Gettysburg, known as America’s favorite drive, to Roanoke and Virginia Blue Ridge.

If you have more time, you may wish to first head over to Williamsburg, Virginia to learn more about the first English settlement, and the Revolutionary War.

Then you would pass through Washington DC on your way to New York.

Gettysburg Video

New York City, NY

No trip to the US is complete without a visit to New York City. It is one of our favorite US cities. It’s as big and glitzy and wonderful as you’ve been told.

We stayed in New York for 4 nights at our favorite INNside New York Nomad with interconnecting rooms. It’s perfectly located to most New York attractions.

We checked off the biggest attractions with my parents including a Broadway show: Wicked, which they loved. New York was one of hteir favorite stops on our Dallas to Boston road trip. They were quite enamored.

New York City Videos

Martha’s Vineyard, MA

Even though I expected something different from Martha’s Vineyard, we had a lovely three day stay on this tiny Massachusetts’s island, famous as a celebrity getaway place.

We didn’t see any, but we loved exploring Chappaquiddick and talking about the mystery surrounding Teddy Kennedy and the tragic accident that happened at the bridge here.

Plus we enjoyed walking around the small historical towns, finding the Jaws filming locations, seeing the beautiful cliffs of Aquinnah and a magnificent sunset at Menemsha.

Martha’s Vineyard video

Boston, MA

Ahh Boston, you quickly became one of my favorite US cities. It’s a city of firsts and superlatives!

On the list of firsts in the United States: public park, public school, printing press, newspaper, post office, police force, subway, first full face transplant, chocolate factory, anti-public smoking law, UFO sighting, and brothel.

I loved its beautiful European feel and incredible history. Plus it was super friendly, filled with sports lovers, and a high energy vibe.

We highly recommend the Harvard University tour, the Boston Freedom Trail and a baseball game at Fenway – so iconic!

We spent four nights staying at a lovely apartment rental south of the city.

Raleigh, NC

We of course, ended our Dallas to Boston road trip in Raleigh, North Carolina so my parents could enjoy some downtime from our home.

They LOVE Raleigh so were happy to dive deeper into exploring it.

They then flew home from Raleigh, to LA to Sydney.

You could easily fly back from Boston, or add in more places to visit in your trip.

Multigenerational Travel Tips

Travel with kids can be intense, especially if you homeschool! Throw in some grandparents, and it can be extra crazy.

If you’re traveling with multigenerations, we have you covered with a few tips:

• 17 Tips to plan a Multigenerational Family Vacation
• How to plan a road trip with kids and keep your sanity
• How to survive a road trip with kids and grandparents

We had an incredible road trip through the South East region with my parents. A few years later they are still raving about everything they saw and did.

It was a great experience to have as a family.

Tips for Traveling From Dallas to Boston Road Trip

Before you go, here are a few more tips to help you make this trip smooth.

• Make sure you book accommodation with a parking lot. You might think this is common across America but it’s surprisingly not. If you stay in motels, then there is usually always parking.
• If you are using an RV, make sure that the campsites you book have powered sites.
• Make sure you book tours and attraction tickets in advance. You may find that tours are fully booked if you leave it too late to make a reservation.
• Keep an eye on the weather. It’s not fun driving in thunderstorms!
• Try to plan your driving times when there is daylight. That way you get to see some of the amazing scenes as you drive.
• Download Google Maps. This way you have access to your route when you’re out of data or service.
• Pick up information at the visitor centers. They are a great place to gather maps, local tips and information, as well as book tours and get the lay of the land.

More US Road Trip Ideas

Need more inspiration for a USA road trip? Check out these other guides…

• 19 Essential things to know before visiting the USA
• How to plan your dream USA trip of a lifetime
• USA tipping guide – how much and when
• 7 Helpful tips for a New England road trip in the Fall
• 7 Great Pacific Northwest road trip ideas
• Places to visit on a South East Coast Road Trip (North Carolina to Florida)
• 18 Fantastic things to do on a Natural North Florida road trip
• 14 epic adventures in the American Southwest not to miss
• 20 Extraordinary Places to Visit on your Utah road trip
• 30 Incredible Places to visit in California
• 19 of the best USA road trips
• 22 of the best scenic drives in the USA