For me, music and place are inextricably linked. A certain location will forever be tied to certain pieces of music, songs, or full albums. Whether a song is actually playing in the background or if the experience and a song share a similar vibe, music often shapes my most nostalgic memories. John Fahey’s masterful guitar work on the stereo while eating at a hip brunch spot in Brooklyn. Ryan Adams’ “Gold” on the headphones as I wandered through Boston’s Commonwealth Avenue Mall. Or even a certain Shins song playing on repeat at the request of my then five-year-old son, simply driving on roads in Plymouth. These aurally paint vivid scenes of the past. For these nostalgic road trips, a certain drivable route matches with an album that, for me, will be forever inextricably linked.
Route 6A – Red House Painters “Ocean Beach”

Now, being stuck in a traffic jam doesn’t seem too nostalgic, but for me it does. Driving Route 6A home from a Cape Cod Fourth of July weekend vacation took forever. Crawling through the towns of Barnstable and Sandwich with the Red House Painters’ classic “Ocean Beach” is a mix of summer and sadness. Its sweeping melodies roll like ocean waves but with a forlorn undercurrent that fits the mood perfectly. The trip was over, but here, on the quintessential Cape Cod road, the moment is still there; it’s still summer. Since then, “Ocean Beach” has been synonymous with the winding Route 6A and its sandy beaches and coastal charm, knowing that this moment won’t last forever, but basking in its serenity now.
Back roads of eastern Connecticut- Lisbon, Canterbury, Scotland – Modest Mouse “This is a Long Drive For Someone with Nothing to Think About”
This Modest Mouse record is the ultimate road trip album for me, even if that road trip was literally in my backyard, driving seemingly nowhere. Seventeen years old, recently behind the wheel, I had two go-to cassette tapes. One was a mix tape with tracks from the Modern Lovers, the Rolling Stones, and the Skyliners (I know, odd choice), the other was this album.

Taken track by track, it may not be my favorite Modest Mouse album, but on the whole, and for its meaning in my life, it is. The cassette I recorded this album onto was 90 minutes long, and the Modest Mouse album was only 74. I fit two Sonic Youth songs and somehow put the first track on the album, “Dramamine,” on there twice, so there was no space on the second side of the tape. I never knew the song names but it didn’t matter; wherever the tape was played, it was perfect.

Driving alone or with friends down the twisty, turny backroads of Northeastern Connecticut, through tiny towns such as Lisbon, Canterbury, and Scotland, “Long Drive” proved to be the perfect soundtrack. Even today, when I hear it, I’m seventeen again, in that blue 1989 Mercury Tracer, with no particular place to go.
Route 169 in Woodstock, CT – George Winston’s “Autumn” and other seasonal albums
When I was in college, Route 169 made me nostalgic for my youth. Then, when I was in my 20s, this road made me nostalgic for my college years. When I was in my 30s… You can see where this is going. As a kid, my family would often travel this road to visit my grandmother every other Sunday, or while we were visiting, drive it for a ride or to grab a bite to eat.

Even back then, I knew this road was special. From Norwich to the Massachusetts border in Woodstock, Route 169 is simply sublime. Its bucolic New England charm is reminiscent of Vermont sans the mountains. Driving it in my college and later years, the perfect soundtrack has been folk pianist George Winston’s seasonal albums, especially “Autumn,” to me, his masterpiece, as I would try to plan a visit to this National Scenic Byway when the season’s colors were on full display.

As it became more difficult to schedule an annual autumn pilgrimage on Route 169, I would find myself there during sporadic points of the year, be it for a book reading or for something else. Luckily, Winston’s “Summer,” “December,” and “Winter into Spring” would provide the soundtrack for any season I was there. But in the autumn, listen to the first haunting notes of “Colors/Dance” while driving by a stone wall shaded by a maple tree in full color in Woodstock, and there’s nothing quite as seasonally spectacular as this.
Summer seaside towns – Bruce Springsteen “Greetings From Asbury Park, NJ”
I was car-less for much of the school year while a college student in Boston. During the last semester of my senior year, I found myself attending classes two days a week and working on an independent study for the other three days, for which I needed wheels to get around. Using the car not just for research, I distinctly remember on one of those first warm spring evenings, heading up to Hampton Beach, New Hampshire, driving north of Boston on Route 1 through Saugus with “Greetings from Asbury Park” playing on the cassette deck and the windows rolled down, feeling hints of the sea breeze. Similar to the Modest Mouse album, it didn’t matter the track, but Bruce’s debut album became the soundtrack of those first warm days.

Fast forward many years, and it’s still the record that I turn to on those first warm summery days. Whether it’s a drive on Cape Cod’s bustling Route 28, on a backroad to a seafood stand, or taking the kids to a carousel at New London’s Ocean Beach Park, this album captures that vibe completely. Although the seaside surroundings may be similar to the Red House Painters, the essence is worlds apart. “Ocean Beach” by Red House Painters is seagrass gently blowing in the wind with the ocean just beyond; it’s stately colonials and hydrangeas. “Greetings From Asbury Park” is the smell of fried food, incessant revving of motorcycles, and souvenir t-shirt shops. It’s the closest thing to the Jersey Shore that we have in New England.

Interstate 91, Route 5 in South Deerfield, MA – Vince Guaraldi Trio “A Charlie Brown Christmas”

As a true Backyard Road Tripper, the thought of feeling nostalgic about an interstate seems quite far-fetched. Whether traveling from Connecticut or the Boston area, I’d often make a journey to the Yankee Candle Village in South Deerfield, MA, especially in late fall or early winter. It was a way to ring in the Christmas season. Driving on Interstate 91 north, once past Springfield, the traffic starts to thin out, and the terrain becomes hilly. We’re not quite in the mountains, but there are enough impressive views to give it that feel. Once this region came into view, the Vince Guaraldi Trio’s “A Charlie Brown Christmas” soundtrack to the television special fit the mood perfectly. Mostly instrumental, it provides a jazzy holiday feel. Couple the album with the views and the awaiting destination of the Yankee Candle Factory, and it was the perfect trip for all senses.

For these nostalgic backyard road trips, the music and the place are forever linked. Whether it’s warm-weather daytripping to the sounds of Bruce Springsteen and the Red House Painters, or interstate highway driving to Vince Guaraldi in the weeks leading up to Christmas, these five albums provide the essential soundtrack for these nostalgic backyard road trips.
