A 4-Week Dallas to Boston Road Trip Itinerary

A four week road trip is not something many Americans will take. I was surprised when we were traveling this route with my parents to meet an Australian family who were doing the same thing.

Like my parents, they flew into Dallas, rented a car, and were making their way across the Southeast. I loved hearing this.

USA road trip mini van
Our Kia Sedona – great family road trip van!

So many Australians fly into LA and do the boring standard Disneyland, Las Vegas, Grand Canyon route.

I mean, i get it, they can be cool places to visit in the USA, but we think it has waaaay better than that. So much of the cool things can be found in the Southeast USA region.

It has loads of culture and history, beautiful beaches, fun festivals, great food and friendly people.

We’re excited that more Australians and international travelers are considering this kind of road trip. It’s easy for an Australian as you can fly direct to Dallas.

Fly into Dallas from Australia

As a family who has flown to the USA from Australia multiple times through different cities, we can tell you Dallas is our favorite. We get through immigration faster, there are more connecting flights at decent times, and, for us, its closer to the East Coast, where we mostly go.

We’d much prefer to do the longer flight first, and then only have one connecting flight to get to our final destination.

If you fly into Dallas, as this road trip from Dallas to Boston will show you, you will have access to many cool spots in the South East region.

Our Six Week Road Trip

Brazos River Waco Texas Fixer Upper location
My Mum and I in Waco, Texas

My parents wanted to come visit us, as we had recently moved (again) to Raleigh, North Carolina.

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 you could do with any length of time. Adjust as you see fit. You could go slower and take several months, adding in more places – 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.

Minnesota Start

Prince mural in Minneapolis
Prince mural in Bloomington, MN

We’re starting the first ten days of the trip driving to Bloomington, Minnesota and exploring the Mall of America and a few other cool things to do there, including 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.

Multigenerational Travel tips

magnolia bakery Fixer upper Waco texas
Cupcakes with Nan and Pop

Travel with kids can be intense, especiall if you roadschool!

Throw in some grandparents, and it can be extra crazy. We have you covered with a few tips:

We had an incredibe 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.

Dallas to Boston Road Trip

Slave house Carnton House Civil War Tour
Slave House, Franklin TN

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. You may even want to detour to New Orleans.

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

For each place listed below, we have linked to our in-depth blog post on that place or experience with all the tips you need to have a great time there.

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

Saving 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. 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.

Dallas, Texas

JFK Dallas museum
JFK Museum

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.

Read More: The JFK Museum Dallas

Waco, Texas

magnolia table restaurant waco tx
Breakfast at Magnolia Table

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!

You can read more in our post on the Magnolia Experience in Waco Texas

Waco Video:

San Antonio, Texas

arched bridge san antonio-river walk texas
San Antonio River Walk

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.

Read more:

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, Louisana

Mardi Gras in New Orleans
Mardi Gras with kids

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. (click the links in this sentence for posts on all those places!) You could pick up our North Carolina to Florida road trip plan to head up North via that way. I absolutely love Tennessee though!

Read more posts on New Oreleans:

New Orleans Video

Memphis, Tennessee

Graceland - one of the best things to do in Memphis with kids

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.

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.

One of the best Graceland Tours to do is the VIP Graceland tour. The VIP ticket allows you to skip the queues and gives you access to VIP only museum exhibits, and access to his customized airplanes.

Read our posts with in-depth tips on Memphis:

Memphis Video

Nashville, Tennessee

Family photo before the Grand Ole Opry Show in Nashville, Tennessee
Family photo before the Grand Ole Opry Show

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 stayed here for three nights, renting an Airbnb in East Nashville.

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, Johnny Cash Museum, Patsy Cline Museum, 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!

Read more tips about Nashville:

Nashville Video

Franklin, Tennessee

people standing in front of a house
In Franklin, Tennessee

While in Nashville, you can take a easy day trip to Franklin, TN, a small charming Southern town 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.

Read more: 6 Captivating things to do in Franklin, TN


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!)

These posts will help:

Biltmore Estate, Asheville NC

the biltmore estate north carolina
The Biltmore Estate!

I knew my parents would love the opulence of Biltmore Estate, 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.

 You can buy admission tickets with an all inclusive lunch through our partner Viator.

Read More: The Biltmore Estate in North Carolina

Lake Lure, NC

Lake Lure North Carolina
Lake Lure

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).

Read more:

Lake Lure Video

Gettysburg, PA

gettysburg battlefields tour guided auto tour
Our informative Gettysburg battlefield tour

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.

Read more in-depth tips:

To consider:

You could drive through the scenic Blue Ridge Parkway on the way to Gettysburg, known as America’s favorite drive. You can read some tip son this post on things to do in 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

Brooklyn Bridge NYC
New York is great any time of the year. Our Christmas vacation to NYC

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.

We have a ton of content to help you with your New York travel planning.

See all New York City posts here.

New York City Videos

Martha’s Vineyard, MA

Edgartown Lighthouse, Martha's Vineyard

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.

Read more: 8 Things to do in Martha’s Vineyard

Martha’s Vineyard video

Boston, MA

people walking through a park

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 America: 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! Our posts below have so many good suggestions to enjoy this city of Firsts.

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

See all our in-depth tips here.

Raleigh, NC

make money travel blogging
Raleigh Durham!

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.

Here are a few tips on Raleigh Durham area

More US Travel Trips and Road Trip Ideas

What are some of your favorite places to visit on a Dallas to Boston road trip?

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