Day Trippin’ – Strange Galesvillle, Maryland – A “No Stoplight” Town

Open Sundays 1 – 4 p.m.

One-stoplight towns are tiny. In Strange Galesville, Maryland, I have discovered the elusive “no-stoplight” town.

Galesville is a strange and magical place, with its one main street and a handful of side streets that dead-end at the edge of the water. There is one way in and one way out unless you leave by boat.

The gem of Galesville is where the main street ends at the marina. You can’t miss it. You drive until you can’t drive anymore (about 3 miles), unless you are driving one of those land/water Duck Boats, in which case you can keep right on driving right into the West River.


Here you will find Pirate’s Cove.

The tiny Inn has 5 rooms.

Pirate’s Cove is a combination bar, restaurant, and inn that has been around since the 1960’s. They have sailboat races every Wednesday evening in the summer. There is plentiful indoor and outdoor seating with million dollar views. At the other end of the parking lot is Thursdays, an old steamboat docking station at the end of a pier that has been a restaurant since the 1930’s. There is almost more charm than oxygen in the air with the massive gathering of sailboats floating peacefully on the water and did I mention the view?

The View

Galesville has a fascinating history that begins with Algonquin Native Americans, includes a 1600’s Quaker meeting house and cemetery, and was the site of a freed-slave African American community in the 1800’s. Seriously, this little speck in the road has a story to tell. You can learn all about it at the Galesville Heritage Museum.


Dotted along the main street are several antique and junk shops and a minuscule art gallery.

Suitcases $15 – $50 at Re-Find

Re-Find and River Gallery share a building but have separate entrances. Re-Find is a nice little shop with clean, charming displays that can legitimately call itself an antique store. They are only open the first weekend of every month! Don’t forget to go out back and see what they have under the tent.

River Gallery is an even tinier shop with a changing exhibition ranging from fiber and metal arts to paintings and glass jewelry. Items aren’t cheap, but they are affordable. I am lusting after a chunky, art-glass bracelet that I may have to go back for.


River Gallery

Captain Harvey’s Antiques and Collectibles, located in a 1902 grocery store, is a junk shop, plain and simple, but it is certainly worth a look around. Those shadowy, dusty shops are often where treasures lurk in dark corners. Captain Harvey’s also offers yard sale space for $15 on the weekends. There was only one sale the day I visited, but there may be more treasure hunting opportunities when you go.

Captain Harvey’s Antiques

Galesville Crossing is also a junk shop, like an indoor yard sale, but bigger and brighter than Captain Harvey’s and the only place that I made purchases on this visit. I bought a Pillsbury Dough Boy ($5) because “why not?” (Don’t judge me) and a vintage necklace for $5.


Remember me?
Don’t be jealous.

Scary Dolls

Galesville Crossing has something for everyone. In the market for satanic, homicidal dolls? They’ve got ’em!

My name is Talky Tina and I am going to kill you.
Yep. I’m gonna kill you in your sleep.

Or maybe you prefer your possessed dolls with dead eyes hanging on the wall? Look no further than Galesville Crossing.

Creepy Doll Plates

Last but not least, and not technically in Galesville, is Jailhouse Antiques. It sits just across the street from the only entrance into Galesville and it was an actual jail in the 1930’s with the original cell still in the basement to prove it.

Tiny Jail
Tiny Cell

If you have lunch and wander the shops, tiny, Strange Galesville is worth half a day. I guarantee you that you will enjoy the adventure! Tell folks Strange Annapolis sent you!

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