FreshGrass Music Trail
14 nights self-drive holiday from Chicago to Nashville with tickets for FreshGrass roots festival in Bentonville.
Our FreshGrass tour follows historic Route 66 for the first six days before heading south to the Freshgrass festival (either for the full two days or just the final day on Saturday).
FreshGrass is a small Americana Festival that is held in an old Kraft Cheese factory in Bentoville AK which is now a museum and live music venue called The Momentary. The 2025 line-up includes Shakey Graves, Bél;a Fleck and Alison Brown on the Friday and Lukas Nelson and Rosanne Cash with her husband John Leventhal on the Saturday.
Bentonville is where Walmart began and apart from the Walmart Museum the Walton family have bestowed a huge amount of money on the town of Bentonville itself, making it an especially pleasant and interesting small town.
On Sunday 18th our journey continues to Little Rock AK passing though both Fayetteville AK and Hot Springs AK before an overnight in Little Rock.
Little Rock houses the exceptional William J Clinton Presidential Library, the Arkansas State Capital, and The Little Rock Central High School.
Monday and Tuesday are spent in Memphis TN visiting Graceland, Beale St, etc
The final three days are in Nashville TN before your direct BA flight back to the UK.
Even without FreshGrass this tour combines an unusual and interesting blend of of big City USA, Route 66, Rural Arkansas, one of the most interesting and well planned Presidential Libraries, and the iconic Memphis and Nashville visits. Unique to Route Trip USA, our travel expert Walter Wolfe has visited all the stops and will be doing this trip himself in 2025.
Remember - All our holidays can be shortened or extra nights added or modified with upgraded hotels, car etc. We love building tailor made road trip holidays!
Fly into Chicago and
out of Nashville
1200 miles
approx
Includes flights, car & accommodation
Includes 2 day FreshGrass Tickets
Our 14 Night FreshGrass & Music Trail holiday starts in Chicago and ends in Nashville: Chicago (3 nights), Springfield IL (1 night), St Louis (1 night), Springfield, MO ( 1 night), Bentonville (2 nights), Memphis (2 nights) and Nashville (3 nights)
Your Itinerary
Days 1 - 3:
Chicago (3 nights)
Arrive in the Windy City and spend your first 3 nights in Chicago. Our recommendations include the Willis Tower, the second tallest building in the USA and the “magnificent mile”.
Collect
Car
Chicago,
IL
4 Star
Hotel
Day 4:
Springfield, Illinois
Today you’ll start your adventure by retracing historic Route 66 from Chicago, through rural Illinois and into Springfield where Abraham Lincoln lived prior to his presidency. You can visit his home and burial places.
200
miles
Springfield,
IL
4 star
Inn
Day 5:
St Louis
There's just 100 miles to drive to St Louis, known as the Gateway to the West. You’ll be able to drive a short section of the original brick Route 66 in Auburn, Illinois before walking the “Chain of Rocks” bridge, opened in 1929 to take traffic over the Mississippi River.
100
miles
St Louis,
MO
3 Star
Hotel
Day 6:
Springfield, Missouri
You’re heading through the Ozark Mountains today towards Springfield in Missouri where, in 1926 a road linking Chicago and Los Angeles was agreed. Originally planned as Route 60, but was finally designated as Route 66. Springfield is known as the birthplace of Route 66.
215
miles
Springfield,
MO
Historic
Hotel
Days 7 & 8:
Freshgrass @ Bentonville (2 nights)
Visit the Bonnie & Clyde hideout in Joplin before leaving Route 66 and heading south to Bentonville, the home of Walmart. We recommend staying two nights to enjoy both FreshGrass festival days, tickets are included. If you only want to go for the Saturday, just let us know.
125
miles
Bentonville,
AK
3 Star
Hotel
Day 9:
Little Rock
Today you will pass though both Fayetteville and Hot Springs before an overnight in Little Rock, Arkansas.
Little Rock houses the exceptional William J Clinton Presidential Library, the Arkansas State Capital, and The Little Rock Central High School.
215
miles
Little
Rock, AK
4 Star
Hotel
Days 10 & 11:
Memphis (2 nights)
For the next two nights you’ll be in Memphis, not only famous for Blues but also as the home of Elvis. Attractions include the site of Martin Luther King Jr’s assassination, Sun Studio; often thought of as the birthplace of Rock n Roll and of course Elvis’ Graceland. Food? BBQ of course!
215
miles
Memphis,
TN
4 Star
Hotel
Days 12 - 14:
Nashville (3 nights)
It’s onto Nashville; the home of country music for your final 3 nights. Major attractions include the Country Music Hall of Fame, historic RCA Studio B and the Johnny Cash Museum. In the evenings head downtown to watch live music and you must watch a show at the Grand Ole Opry!
140
miles
Nashville,
TN
4 Star
Hotel
Days 15 & 16:
Nashville & Fly Home
Enjoy the full morning in Nashville, maybe see a few attractions or do a little shopping. This evening you’ll catch your overnight flight back to the UK.
Return
Car
Fly
Home
Fancy an upgrade?
Car
Our standard prices include a small family car, but you can hire a convertible or SUV. Take a look at your car choice here.
Hotels
We are completely independent and have a wide choice of hotels. We can upgrade some or all of your hotels. Just ask us!
All per person prices (pp) shown on this website are based on two adults sharing. Where hotel ratings are shown, these are US ratings, half stars are rounded up to the next full star. RouteTrip USA and RouteTrip are registered trademarks of RouteTrip USA Ltd. *T&Cs Apply. **On most full packages subject to availability. ***Free mobile data is included for most packages during your USA or Canada holiday and subject to usage limits.