The B-side was Better!
Ocean City nor’easter, 2026
I had a completely different September blog post planned. This was to be the Mixtape portion of our Maps. Memories. Mixtapes. programming as we were headed to Oceans Calling Music Festival in Ocean City, MD. Goo Goo Dolls, Mumford & Sons, Ludacris, and a slew of GenX greatness.
The nor’easter yanked the cassette right out of our player, and the concert was canceled.
But thankfully, we had a happy travel accident. On the way into Ocean City, we stopped in Annapolis for lunch, our first visit to Maryland’s capital, and let me tell you, it is a great, historic American town.
This is a lesson on why 50x50 deserves multiple rounds. You may have reached the goal, but there’s so much more after the finish line. But I digress. The point is, we abandoned the rising floodwaters in Ocean City and went back to Annapolis.
Now let’s rewind: 📼
Earlier in the day we had lunch at The Preserve. This name is literal—the restaurant pickles and preserves many of its farm-fresh ingredients. Our server, who was an avid concertgoer himself, recommended a menu to heal our souls the day the music died: Crispy Kale (I could seriously eat it all day), “The Whisky Drink” (Sweet potato, pistachio seasonal deliciousness that I could also sip all day), and an Angus burger with fresh cut fries. We couldn’t give a higher recommendation for the service, atmosphere, and fresh food. Give it a try if you’re in town.
We then wandered Annapolis.
It immediately felt like somewhere we should have visited years ago: brick streets and old buildings, educational statues, military pride, architectural history & QR code tours, Irish roots aplenty, fantastic shops, and the water just beyond it all circled by listing and lulling boats. Very Autumnal and very Eastern Seaboard.
Speaking of Autumn…
Route 404 is the Farmstand Jackpot 🎃
After our spontaneous stop we continued toward the beach, crossing the Chesapeake Bay Bridge—a 4.3 mile dual span bridge with panoramic views of the water—and discovered another happy win. You may think that the most interesting thing about this area is that it takes you through Delaware to get from Annapolis, MD to Ocean City, MD (you read that correctly, Maryland → Delaware → Maryland) but no, it's the produce!
If you take the Route 404/US 113 beach route from the Bay Bridge toward Ocean City, you learn the Delmarva Peninsula is farmland. About 40 minutes after you exit the bridge, you stumble across pumpkins, produce, flowers, homemade goodies and roadside stands every 5 minutes or so. I counted:
Clayton Farms
Ma & Pa's Market
Farmer Gene's Market
Vanderwende's Creamery
Adams Fruit Market
Little Wagon Produce…And
T.S. Smith & Sons Orchard Point Market
The 1st and the last are a little farther apart, but the middle markets are stacked together like a CD tower. Had I known what I was getting into, I would have allotted an extra hour, possibly two. My camera roll began looking like Linus had finally found the Great Pumpkin. I couldn’t have been happier.
Though we enjoyed that ride and made it to our original destination, the waves were wild, we sensed danger, and the ocean was no longer calling, but instead yelling at us to go back.
So we did.
🚗 Back along the farmstand route, grabbing one more hot Pumpkin Spice coffee and donut from the “RoFo” gas station for the road, where I was the weirdo stopping at the now closed stands still taking pictures of the gorgeous fall displays because they made me smile.
🚗 Back across the Chesapeake Bay Bridge, this time after sunset, with ship shadows in the distance holding bright lights on their masts against the inky water like stars in the night sky.
🚗 Back to Annapolis. We had a lovely dinner and readied ourselves for our newly booked next-day flight home. But not before one more really cool morning surprise. I discovered the B side of mother nature’s curated Mixtape.
Breakfast was waterfront surrounded by boats (both real and models), and we were the only guests in the restaurant at 7am before heading back to Dulles. After ordering, the staff turned on the ambient music, which turned out to be a completely inspired playlist, so I’m sharing the ones I remember with you now:
Stormy Weather - Etta James
Bewitched, Bothered and Bewildered - Sinéad O’Connor
La Vie en Rose - Louis Armstrong
One Fine Thing - Harry Connick, Jr.
Autumn Leaves - Nat King Cole
Nuages - Django Reinhardt
Stella by Starlight - Miles Davis, John Coltrane, Bill Evans
And finally, we took our coffee to the balcony for one last look at the choppy waters, and got our actual live music: The U.S. Naval Academy observes Morning Colors every day. At 7:55 a.m., First Call to Colors is sounded; at 8:00 comes Attention and the raising of the flag. I am so grateful to have logged the memory of that haunting bugle across the harbor, opening the day—and, once again, my eyes— to the amazing country in which we live.
So Maybe the Wrong Trip Was the Right One
I started the weekend thinking September's story would be about a music festival.
Instead, the mixtape became sailboats knocking gently against the docks, a Navy bugle carrying over a historic city, tires rolling down Route 404, and probably me yelling “PUMPKINS!” every three miles.
And I like this story better.
The big things are wonderful. Book the concert. Make the reservation. Plan the itinerary. But don't become so attached that you miss what happens when all of it inevitably changes.
A new city. A new view. A new sound.
That's why 50x50 is never really about checking off 50 states. It's about whatever state you’re in. To quote one of my favorite songs:
“Been talkin’ bout the way things change.
And my family lives in a different state…”
~ Rivers and Roads, The Head and the Heart
(Which, sadly, was on the Oceans Calling lineup we never got to hear. No, we haven’t met them and they are not endorsing our business. If they see this…call us! 😉)
So we’ve covered Mixtapes, we’ve covered Memories. Speaking of Maps…
There’s another adventure we’ve been quietly building behind the scenes: the 50x50 MapApp & Compass Club are coming to life!
With the MapApp, you’ll be able to track your travels digitally, explore stories and trip recommendations for all 50 states, and play the License Plate Game along the way.
Want to go deeper? Compass Club—our working name for the premium experience—will be a one-time purchase, no subscription required app, with a customizable digital travel scrapbook, personal trip planner, additional games to help you learn about the amazing USA, and even more ways to build the stories and soundtracks behind your states.
I’ll share much more in October, including a peek at where the app is headed, what we ultimately decide to call everything, and how it all grows into the bigger 50x50 experience.
And if you happen to be in Florida, come see us at Port St. Lucie Oktoberfest on October 3 from 5–9 p.m.! We’ll have the gear, the app, and plenty to talk about as this next chapter of 50x50 begins.
~Safe Travels ❤️
