Trips & Routes

Small Towns

Trips & Routes
Small Towns

This Little-Known Waterfront Town Is One of the Most Charming in Maryland

Located on the Choptank River, Cambridge is a little-known waterfront town in Maryland home to stunning lighthouses and historic streets.

by Raymond Goldfield
on Apr 13
The Choptank River Lighthouse in Cambridge, Maryland at night, illuminating the river.
Trips & Routes

The Bayfront Maryland Town Locals Hope Stays Off Tourists’ Radar

by Raymond Goldfield
on Mar 10
A small town square with a town map reading "Leonardtown" and a cardboard cutout figure smiling next to it.
Trips & Routes

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

by Charlie Boyle
on Feb 1
An orange sunset glows over the outline of a coastal town with residences sitting right next to the water. The water remains still to a point of near perfect reflection.
Trips & Routes

The Small Town in Maryland That Feels Straight Out Of ‘Wedding Crashers’

by Jacki Mick
on Dec 13
A bright sunset over the water, seen across the metal railing of what appears to be a bridge or causeway.
Trips & Routes

Escape to This Charming Mountain Town in Maryland Before Fall Ends

by Melanie Johnson
on Sep 29
A historic covered bridge surrounded by fall foliage and a flowing creek in Thurmont, a mountain town in Maryland

Latest Small Towns

Trips & Routes
Small Towns

This Tiny Town in Maryland Feels Like a Living Time Capsule

With historic landmarks, a quaint district and quirky festivals, this tiny community in Maryland is frozen in time.

by Melanie Johnson
on Jan 9
exterior of st. bartholmew's church in laytonsville maryland
Trips & Routes
Small Towns

The Remote Town in Maryland We Simply Can’t Get Enough Of

Take in sparkling views of Chesapeake Bay, plenty of seafood, and a healthy dose of maritime history on this small island.

by Kate Kolenda
on Apr 3
Blue sky over a waterfront view from Solomons Island MD.
Trips & Routes
Small Towns

Skip Europe This Summer: This Island in Maryland Is Just as Peaceful as the Wadden Islands in the Netherlands

Skip the flight to Europe—Smith Island in Maryland feels like the Wadden Islands in the Netherlands, with car-free streets, fresh seafood, and water views.

by Jasmine Vieau
on Jun 30
A vibrant sunset over the tidal marshes and winding creeks of Smith Island, with golden light reflecting on the water.
Trips & Routes
Small Towns

The Walkable Maryland Town That’s Known for Its Waterfront Views

Stroll along Main Street in Annapolis, a charming, walkable town in Maryland, perfect for a day trip or a weekend getaway.

by Beth Price-Williams
on Dec 23
Strung lights illuminate a historic Annapolis street at night, viewed through an open iron gate framed by large trees.
Trips & Routes
Day Trips
Small Towns

If You Only Have One Day to Visit This Small Town in Maryland, Here’s Everything You Absolutely Can’t Miss

Explore Emmitsburg, a small town in Maryland with historic sites, local dining, and hiking in Catoctin Mountain Park.

by Jasmine Vieau
on Nov 13
Dome of the Basilica at the National Shrine of Saint Elizabeth Ann Seton in Emmitsburg, Maryland