What happens when you start in one of America’s oldest cities, point the cars south, and avoid taking the easy way to Nashville? You get one of our most diverse AFR Rally routes.
The Boston to Nashville Grand Tour took us from the historic streets of Boston through Rhode Island and Connecticut, across Long Island by ferry, into the middle of Manhattan, through Washington D.C., across the Shenandoah Valley, into the mountains of Virginia and North Carolina, and eventually onto one of America’s most famous driving roads: Tail of the Dragon.
The finish line? Downtown Nashville.
This wasn’t designed to be the fastest route from Boston to Tennessee. It was designed around the places, roads and experiences worth stopping for along the way.
Day 0 – Boston
Before putting any serious miles on the cars, we started with a night in Boston. Staying at the InterContinental Boston put us right in the middle of the city and gave everyone a chance to arrive, get settled and spend the evening exploring.
Boston is a great starting point for a road trip because the trip begins before you ever leave the city. Historic neighborhoods, waterfront areas, old architecture, bars and restaurants are all within walking distance. Oh yea we went and saw the Red Sox play the Yankees!
Walk around. See some history. Find a bar. Have dinner.
Day 1 – Boston to New York City
6-7 Hours | 250 Miles
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- Boston to Cross Sound Ferry, New London – https://maps.app.goo.gl/h8wHLuYaomUgsSFM7
- Cross Sound Ferry, Orient Point to New York City – https://maps.app.goo.gl/ZdppHcy4nYN66Cad8
Our first driving day would take us approximately 250 miles, but this wasn’t going to be a normal highway run. We departed Boston early and made our way through the city’s underground highway tunnels before heading south toward Providence, Rhode Island. From Rhode Island, we continued along the coast toward New London, Connecticut.
That’s where the first unusual part of the route began. Instead of following the highways toward New York City, we drove directly onto a ferry. At New London, we boarded the Cross Sound Ferry for the trip across Long Island Sound to Orient Point. Loading a group of rally cars onto a ferry isn’t something you get to do on most road trips, and that’s exactly why we wanted it in the route. After crossing the Sound, we rolled off the ferry onto the eastern end of Long Island. Suddenly the drive had an entirely different character.
Instead of interstate highways and major cities, we were driving through Long Island’s North Fork with its small towns, farms and vineyards.
There are easier places to take a group of cars than Manhattan. That’s also part of the fun. After the relative calm of eastern Long Island, we headed directly into New York City and checked into The Michelangelo Hotel in Midtown. They had good underground parking which even our low cars could get into no issues. Now its time to experience everything in New York from Central Park, to amazing food, and just walking around to see the sites.
Day 2 – New York City to Washington D.C.
5 Hours 47 Mins | 260 Miles – https://maps.app.goo.gl/NwRrnuDJMf5LR9q36
We left Manhattan early, incorporating a few iconic New York landmarks into the drive as we headed south. The route took us past the Empire State Building and through Lower Manhattan near the 9/11 Memorial before finally escaping the city.
From there, we continued south through the Mid-Atlantic toward Washington D.C. This section wasn’t about finding the twistiest road possible. It was about connecting two of America’s most important cities and experiencing just how dramatically the scenery and atmosphere change as you travel south. The roads took us through New Jersey, skated the outskirts of Philadelphia, and then on to Maryland where we crossed over part of the Chesapeake Bay into Annapolis where we took a break for lunch. Shortly thereafter we were rolling into the south side of DC where we checked into the Kimpton Hotel Monaco, giving us a central base for exploring the city without needing the cars again that evening. After spending the late afternoon walking around Washington’s monuments and historic sites, we finished the day with dinner at The Hamilton.
Day 3 – Washington D.C. to Smith Mountain Lake Virginia
5 Hours 20 Mins | 250 Miles – https://maps.app.goo.gl/bfPvhiwya4E4SH2X9
Leaving Washington and the cities behind, we pointed west toward Virginia and Luray Caverns. Heading south through the Shenandoah Valley had us driving through epic backcountry 2 lane roads. The Shenandoah Valley is one of America’s great road-trip destinations. Probably the BEST driving road is Blue Ridge Parkway. 469 miles of road from Virginia to North Carolina. Mountain ridges stretch into the distance, scenic overlooks appear along the route, and the region is filled with small towns and historic locations. It is also an area deeply connected to American Civil War history, with numerous battlefields and historic sites scattered throughout the valley.
This part of the country is sparse for big fancy resorts and hotels. So we decided to check out Smith Mountain Lake which is known for its vacation lake life atmosphere. We stayed at Bedford Landings which was a Bed and Breakfast on the East side of the lake. It featured 4 rooms and a large property at an airfield. A short drive away are restaurants and shops to visit. The next morning, we were back on the road early to head into Nascar country.
Day 4 – Smith Mountain Lake, VA to Little Switzerland, NC
6 Hours 30 Mins | 290 Miles – https://maps.app.goo.gl/iRJ3o8ocikuGtg9S8
From Smith Mountain Lake, we headed south using the backroads of Virginia toward Winston-Salem, North Carolina. This was one of those days where the route mattered more than any single attraction. Smaller highways and rural roads carried us south as we worked our way toward one of the most important regions in American motorsports.
Our next stop was a little bit of VIP treatment from a friend in Mooresville, North Carolina. Often called “Race City USA,” Mooresville and the surrounding area are home to an incredible concentration of NASCAR teams, race shops and motorsports businesses. For our stop, we headed to Penske Racing for a tour and lunch. For those that don’t know someone there, you can stop and see the race shop from an overlook and visit their gift shop.
But we weren’t done for the day. From Mooresville, we turned back toward the mountains and continued on to our destination for the night, Little Switzerland, North Carolina. Named for the surrounding mountain scenery, Little Switzerland sits along the Blue Ridge Parkway and has long been a favorite destination for drivers and motorcyclists exploring western North Carolina. We stayed at the Skyline Village Inn, putting us right in the mountains and perfectly positioned for what was coming the following morning. Because Day Five contained the road everyone had been waiting for.
Day 5 – Little Switzerland, NC to Nashville, TN with Tail of the Dragon
8 Hours | 375 Miles – https://maps.app.goo.gl/mhFjGdTPzu3hKmq68
This is a mega day of travel to get to one of the most famous driving roads ever. 318 curves in 11 miles. That’s the number that made this stretch of road famous. US Route 129 along the Tennessee-North Carolina border is better known simply as Tail of the Dragon. There are no intersections or driveways along the legendary section—just corner after corner after corner. For enthusiasts, it’s a destination in itself.
We headed there early, giving ourselves time to experience the road, stop for photos and enjoy the atmosphere surrounding one of America’s most famous automotive playgrounds. The Dragon demands respect. Tight corners, blind turns, motorcycles, other enthusiast cars and changing conditions mean this isn’t somewhere to chase lap times.
For AFR, Tail of the Dragon was the natural climax of the driving portion of the trip. But we still had one destination left to get to. After days of historic cities, ferries, mountain roads, scenic overlooks, motorsports stops and hundreds upon hundreds of curves, we pointed the cars west toward Nashville, Tennessee.
The arrival in Nashville marked the end of approximately 1,400 miles of driving. We checked into the Hilton Nashville Downtown for two nights, parked the cars and, for the first time since Boston, didn’t have an early departure looming the following morning.
We spent the day exploring downtown, finding somewhere for brunch, listening to live music, shopping for boots and experiencing the bars and restaurants that have made Nashville one of America’s most popular entertainment destinations. After five consecutive days on the road, having a full day with nowhere else to be was the perfect way to end the trip.
The following day, the cars were loaded on a transport truck, and everyone flew home.
Planning a Boston to Nashville Road Trip
You could drive from Boston to Nashville much faster than we did.
But you’d miss the point.
The appeal of this route is how many completely different experiences can be connected into a single road trip.
You begin surrounded by the history of Boston.
The next day your car is sitting on a ferry crossing Long Island Sound.
A few hours later, you’re driving into Manhattan.
Then you’re standing in front of the monuments of Washington D.C.
A day later, you’re surrounded by the Blue Ridge Mountains and Shenandoah Valley.
Then you’re visiting the heart of American motorsports in North Carolina.
And finally, you’re carving through Appalachian mountain roads on your way to Tail of the Dragon before finishing among the honky-tonks and live music of Nashville.
How Long Should You Take?
We built this route around approximately five major driving days, followed by a full day in Nashville.
That pace worked well because most days were roughly 250–375 miles.
On paper, 250 miles doesn’t sound particularly demanding.
But there’s a major difference between covering 250 interstate miles and spending the day stopping at attractions, driving mountain roads, navigating cities and exploring along the way.
Give yourself time.
The entire reason to take this route instead of the interstate is to experience what lies between Boston and Nashville.
The Best Part of the Route
It’s difficult to choose one.
For pure driving, Tail of the Dragon is the obvious highlight.
For scenery, the Shenandoah Valley and Blue Ridge Mountains are hard to beat.
For sheer contrast, nothing compares to going from the streets of Manhattan to quiet Virginia mountain roads within a matter of days.
And taking the cars aboard the ferry from Connecticut to Long Island gave the trip a completely different element from a traditional road rally.
That’s ultimately what made this route memorable.
It wasn’t one great road.
It was the combination of completely different experiences.
Why We Drive
AFR Rally routes aren’t designed by asking Google Maps for the fastest way to reach the next hotel.
We want the road trip itself to be the reason for going.
Boston to Nashville delivered exactly that.
We crossed multiple states, drove through some of America’s most historic cities, crossed Long Island Sound by ferry, explored the Shenandoah Valley, visited the heart of NASCAR country, stayed in the Blue Ridge Mountains and drove one of the most famous stretches of pavement in America.
Then we parked the cars in Nashville and celebrated.
There are certainly faster ways to drive from Boston to Nashville.
We’d rather take the interesting one.
