5 Small Towns in Maryland So Dreamy, You’ll Swear You’ve Seen Them on TV

Teeming with hidden gems, Maryland has small towns along the coast, in the mountains, and stretching across the countryside. Many have a charm and beauty of their own, but below are just a few towns that truly seem like something out of a television show and are ready for a spot on your must-visit list.

1. Havre de Grace

Location: Northeastern Maryland

Why It’s So Dreamy: It’s all about the water views in Havre de Grace. Originally named after the French town of Le Havre by French soldiers who passed through during the Revolutionary War, this town has been popular for decades due to its position as a sailing town with many roads stretching outwards from it during colonial times. It has one of the oldest lighthouses on the entire east coast and was actually considered as an option for the capital of the United States at one point in time.

Throughout its history, it has almost been burned down, served as a crossing point on the Underground Railroad, hosted multiple presidents, and even hosted a horse race featuring the famous horse Seabiscuit. Today, it remains a hotspot due to its endearing boardwalk/promenade, museums, and birdwatching potential, yet oddly small in size despite its popularity and charm. 

2. Oakland

Location: Western Maryland

Why It’s So Dreamy: Largely considered a hidden gem, this peaceful town sits in the middle of mountains, forests, and three different state parks. As such, the town has access to all the activities the four seasons offer (fall foliage viewing, winter sports, hiking in the spring, and boating in the summer, etc.). Beyond what the outdoors offers, Oakland is known as a bit of an artsy town with Victorian architecture, quirky local shops, museums, galleries, festivals, and an arts council.

3. Vienna

Location: Eastern Maryland

Why It’s So Dreamy: Founded in the 1700s, this lovely small town on the Nanticoke River has maintained its strong historical ties, giving it a distinct feeling that things here have remained untouched by time. With only a few hundred residents, this is one of the smallest towns on this list, but it’s clear that these locals have put considerable effort into maintaining and preserving the area. It’s quiet and peaceful, surrounded by farmland and marshes with a marina that has become a secret hotspot for fishing. 

4. Bel Air

Location: Central-eastern Maryland close to Baltimore 

Why It’s So Dreamy: This is the town that families wish they could move to. It’s small and close-knit, with a classic Americana tree-lined main street, lots of greenery, historic buildings, a highly rated school system, mom and pop shops, farmers markets, and constant festivals and events aimed at strengthening the community. Additionally, it’s a small town near larger cities, which puts it in a position to offer better shopping and dining than more remote areas can.

5. Boonsboro

Location: Central-western Maryland

Why It’s So Dreamy: This tight-knit community has become locally famous due to the presence and influence of the romance writer Nora Roberts. As of late, the town seems like something out of a Hallmark movie, with dessert shops, adorable restaurants, bookstores, cafes, and more, all on a quaint main street and in a town square. The local inn, in particular, has romance on the brain with rooms dedicated to famous romantic couples found in literature. But for those who aren’t as romantically inclined, the area has many historical sites related to the Civil War (as well as museums) and is at the base of the Appalachian Mountains, with easy access to the Appalachian Trail.

Ready to start planning your next trip? Try Only In Your State’s itinerary planner.