4 States 72 Hours!

My first solo trip is officially in the books! I’m excited to share what I loved, learned, and saw during this wild 72-hour ride.

First, let’s talk about why I went on a solo trip in the first place. It was the weekend after my 23rd birthday, and to be honest, that number felt so boring and I wanted to spice it up. But I also realized I’d been holding myself back from seeing the world just because no one else could experience it with me.

Post-grad life means all of our schedules are different. We live in different states, and even when we’re in the same town, we have different priorities. None of those are bad reasons, they’re just different, and that’s okay. But they shouldn’t stop me from choosing my priority of traveling.

So, I went to Maryland, Delaware, Pennsylvania, and Virginia for the first time by myself!

One of my favorite things about this trip was that I got to choose what I did, and when I did it. Aside from plane tickets, renting a car, and finding a place to stay, there really wasn’t a set plan for each day. No expectations. No pressure to make this trip “perfect”. It was simply time for me to explore places I’d never been before.

Beyond visiting three new states, I also got to end my trip in D.C. (told you I’d be back) and spent my last evening with a best friend in a different place. I am forever grateful to be able to keep up and see my friends that live so far away.

Now let’s break down how I managed to hit all these spots in just 72 hours:

I flew into Virginia (IAD), on October 3rd, grabbed a rental car at the airport, a quick bite on the road, and then drove about three hours to my Airbnb in Port Deposit, Maryland. As someone who drives around Texas a lot, this drive felt totally manageable & easyyyyy. That evening, the town next to mine, Havre De Grace, was throwing their autumn festival, so I spent my time in a local pub with a good book waiting for my night to begin. The festival was a perfect first taste of the town: food vendors, local shops, musicians performing on every street, artists showing off their work, and plenty of locals soaking it all in. Honestly, I can't think of a better way to kick off my trip.

The next morning, I set off for Delaware. Just a 30-minute drive to Newark, with a quick pit stop in Chesapeake Bay on the way, I was in the middle of family weekend at the University of Delaware. I was thrown into the fun chaos of locals and tourists, and I could not have made this day better if I tried. As I walked around downtown, a local acapella group stood outside the library and serenaded the people as they strolled and ate. I popped into several shops, picking up practical souvenirs like jewelry and olive oils, even getting a head start on my parents’ Christmas gifts, and ended my shopping by checking out the Universities library in downtown. To end my time in Newark, I had my first a meal by myself at a local outdoor restaurant. Surprisingly, it wasn’t nearly as awkward as I expected. I brought a book, ate my meal, and listened to the acappella group performing across the street. The food was delicious, and the company of the characters in my book was all I needed.

After I ate, I headed to my final stop of the day: Oxford, Pennsylvania, just a 25-minute drive away. On the way, I made one more stop in Delaware at a local art museum, spending time admiring the paintings and stained glass. Once in Pennsylvania, I wandered downtown, snapping photos and picking up yet another T-shirt to which I was going to have to fit in my suitcase.

By 4 p.m., I was back in my Maryland town and ended the day at a dock for yachts. I watched the water, sketched the ships in front of me, and spent some quiet moments practicing gratitude, thanking God for the chance to experience so much of His creation.

The next morning, I packed my things and got on the road to Annapolis, Maryland, my last new adventure before heading to D.C. I toured the Maryland State House, strolled around downtown, popped into antique stores, and treated myself to some local ice cream. I don’t know why Annapolis isn’t talked about more because it was absolutely perfect. If you love a mix of old charm and new experiences, I couldn’t recommend Annapolis more. Overall, I loved this trip, and I can’t wait to go back to each of these states to explore even more.

I encourage everyone to go on at least one solo trip in their life. Learn how to spend time by yourself, learn the goodness of being bored, and spend some time one-on-one with the creator and His creation!

Below, you will find some of my favorite recommendations and outfits that are perfect for the weather in Maryland, Delaware, Pennsylvania, and Virginia in October!

LETS GO!

Airbnb

• This is the specific Airbnb I used in Maryland. I can confirm as a girl on a solo trip I felt very safe in this town!

  • https://www.airbnb.com/rooms/706717656105162542?search_mode=regular_search&adults=1&check_in=2026-01-11&check_out=2026-01-16&children=0&infants=0&pets=0&source_impression_id=p3_1766773226_P3gMH108MYahhIdQ&previous_page_section_name=1000&federated_search_id=c466a4a5-fe45-4d7c-9ad9-74e0ba23f1b4

Traveling Around

• Driving - If you plan to travel to multiple states, I highly recommend renting a car. It’s usually easiest to pick up and drop off your car at the airport you’re flying into, but do whatever works best for your budget!

  • I used Dollar Car Rental and found an affordable Nissan that fit all my luggage perfectly and it didn’t feel too small on the road.

  • https://www.dollar.com/us/en/deals-and-offers/featured/save-pay-now?gclsrc=aw.ds&gad_source=1&gad_campaignid=2026796378&gbraid=0AAAAAD_PB6EJbtL_qKSNWTtH62D0N8Kjg&gclid=Cj0KCQiAx8PKBhD1ARIsAKsmGbd50ekNaZVlbvVgEFZ6_z5oP8lqFiw8g9JUWS8L8riHCiNMzrpqMnQaAqaDEALw_wcB

• Walking - Once you’re in each town, walking is the easiest way to get around, and it also helps save gas for longer drives between states. I always felt safe walking around Maryland, Delaware, and Pennsylvania, but as always, when traveling solo, I recommend staying alert and aware of your surroundings.

Restaurants

• Coakleys Pub - Havre De Grace, MD

• La Cucina - Havre De Grace, MD

• Caffe Gelato - Newark, DE

• Kilwins Ice Cream - Annapolis, MD

• I got groceries and cooked several meals at the Airbnb to save some $$$!

Coffee Shops

• Java by the Bay - Havre De Grace, MD

• Chesapeake Bay Coffee Co. - Chesapeake Bay, MD

• Old Fox Books - Annapolis, MD

Places to Explore

• Downtown Havre De Grace

• Washington Street Books & Music - one of the most surprising and coolest places!

• The Luckiest Light Art Museum

• Chesapeak Bay Farmers Market

• Downtown Newark

• University of Delaware

• Delaware Art Museum

• Tidewater Marina

• Concord Point Lighthouse

• Maryland State House

• Bookstore of Old Fox Books

• Downtown Annapolis

• Maryland Fedoration of Art

Pictures of the weekend!

What I Wore!