Quaint Towns

If you’re craving charming historic towns, vibrant waterfronts and the simple thrill of spotting an eagle overhead, let me tell you about our recent weekend wandering through some of Maryland’s best-kept gems.  From Chesapeake City to Chestertown to Havre de Grace — with Elkton as our cozy home base — every stop offered its own brand of magic, with plenty of mojitos, music, antiques and awe-inspiring wildlife along the way.

And let’s not forget the journey itself — mile after mile of gorgeous countryside dotted with horse farms, fields of sweet corn and rolling hills that paint a picture of classic Americana at its finest.  It’s the kind of scenery that makes you slow down, roll the windows down and simply soak it all in.

Nestled along the C&D Canal, Chesapeake City was once a bustling 19th-century port vital to shipping between the Chesapeake Bay and Delaware River.  Today, it’s a storybook village where time seems to slow.  Strolling down the quaint streets lined with colorful historic homes, you’ll discover boutique shops, welcoming taverns and friendly locals who are always ready to share a tale or two.

Our favorite spot?  The Chesapeake Inn.  Grab a table on the deck overlooking the canal and watch the parade of boats drift by.  Pair it with their super fresh mojitos, a wood-fired brick oven pizza, or — if you’re up for something delightfully unexpected — their sushi.  The Hairy Chinn roll is something I make sure to get every time I visit. Live bands and DJs often add music to the magic here, creating a vibe that barely kept us in our seats.  Chesapeake City is the perfect first stop to ease into your Maryland waterfront adventure.

Further south on the Susquehanna River, Havre de Grace has stood witness to centuries of American history.  Named by the Marquis de Lafayette after the French port city of Le Havre, this riverside town played a strategic role in the War of 1812 and was once even in the running to become our nation’s capital.

We spent the morning wandering The Cannery, an antique mall that felt like stepping into a living scrapbook.  Among the treasures:  1930’s quilting squares with vintage fabrics begging to become something new and a pile of weathered cedar shakes perfect for future art projects.  I couldn’t help but scoop up little curiosities for my soon-to-be-built “she shed” — so stay tuned for more on that adventure!  The town is filled with a charming mix of old establishments that have stood the test of time and fresh new shops that bring an extra spark of life with a lean into art to its historic streets.

Crossing the Chesapeake City Bridge landed us in Chestertown, a colonial seaport founded in 1706 along the Chester River.  Once a thriving trade hub, today it’s all about quaint streets, charming storefronts and friendly faces. 

First, we popped into their gorgeous visitors center and chatted with Robin, who’s so proud of the town’s history and eager to help personalize your trip; nearby, Washington College — one of the oldest colleges in the nation, founded in 1782 with George Washington himself as one of its early supporters — adds an air of scholarly charm, and the fountain in the center of town is the perfect spot to pause and soak it all in.

We spent a sunny morning browsing local shops before wandering the bustling  Chestertown Farmers’ Market, where we found everything from some of the best kimchi and kraut to heirloom tomatoes and ice cream. Local artists amplify the atmosphere, as sisterly strums and fiddle songs fill the air.   It’s the sort of place where you can sip coffee, sample local liquors and chat with farmers who’ve been tending the same land for generations.

This whole adventure was anchored by our stay in Elkton, nestled in a quiet community that feels worlds away from hustle and bustle.  We always stay with dear “friends like family,” enjoying slow mornings and easy evenings together.   However, there are plenty of Airbnb options near Elkton—from cozy cottages and Mongolian yurts to scenic, upscale homes — whether you’re planning a weekend getaway or an extended visit.

One of our favorite nearby hangouts is UnWined on the Water at Triton Marina.  Think wide-open river views, picnic table seating, two outdoor bars, a sandbox for the kiddos and live bands more often than not — whether it’s a lazy Wednesday evening or a buzzing Saturday night.  Perched on the banks of the Elk River, we watched eagles and egrets drift lazily overhead as fireworks later popped from at least five different spots along the water.  The vibe is pure summertime bliss.  And the food?  The Salmon Chesapeake — perfectly cooked salmon topped with lump crab and a brandy sauce — might just be worth the trip alone.  The eats were only rivaled by the warm, attentive service that makes you feel instantly at home.  Please note:  Out of respect for the community, please make sure to keep your speed to 25 MPH or less on the road to the marina restaurant — many young families call this place home and deserve that consideration.  Treat it like it’s your own neighborhood.

✨ Sometimes the best travel days are slow, meandering and sprinkled with little surprises — like finding the perfect 1930’s fabric, hearing your favorite song by a live band or watching a bald eagle glide overhead.
✨ Eat outside whenever you can — mojitos and sunsets just taste better dockside.
✨ And never underestimate the joy of simply driving through peaceful farmland — rows of corn, grazing horses and classic red barns that remind you how beautiful this country truly is.

If you’re looking for a weekend road trip packed with small-town charm, incredible food and nature at every turn, you might want to start planning your own Maryland waterfront wander.