Six towns on the East Coast you’ll love to love.

One of the things I love about America’s east coast is the beautiful brick-lined coastal towns that make up our historic roots. A few winding roads with colonial houses merge into a main street (often called “Main Street”) with mom-and-pop stores, boutique restaurants, fudge and candy shops, and, always, a great place to get a local t-shirt.

Having grown up in New England, I’ve always loved these mini-cities. There is plenty to do, everything is walkable, and neighbors trust each other. Yet as I’ve lived and traveled around the US, I’ve found that there are many cities that fit the same description — and if you didn’t know any better, you’d think you kept coming back to the same place.

Here are six towns that look incredibly similar to one another, but also sport some unique differences too. If you’re in the mood for a summer road trip, try passing through all of them for a trip down the coast (Estimated time from #1 to #6 is about 16 hours non-stop.):

1. Coastal town #1: Portland, Maine


Have you ever seen a cuter town than Portland? With art shops and moose/lobster paraphernalia up and down every street, you would think you could stay here forever.

Score points with: Freshly thrown pottery and “moose poop” chocolates (Don’t ask; just love).

2. Coastal town #2: Portsmouth, New Hampshire

Photo from
Photo from

Portsmouth is my home city and a place I will never cease to love. Make sure you eat somewhere along the port, like Poco’s Bow Street Cantina or the Old Ferry Landing, and don’t forget to catch a summer concert or play in Prescott Park.

Score points with: A tour of the historic Strawberry Banke, a lobster dinner by the water, and an after-dinner drink at The Red Door.

3. Coastal town #3: Newburyport, Massachusetts

Photo from
Photo from

Just half an hour from Portsmouth, you might think you’re bound to hit the same sights, and if that’s your goal then you probably will. Yet Newburyport has an earthy, soul-seeking vibe that you can find while dining at the Portuguese-influenced Ceia or listening to tunes at The Grog.

Score points with: Seafood at Michael’s Harborside and a show at the Firehouse Center, an old market house that was built in 1823.

4. Coastal town #4: Georgetown, District of Columbia

Wisconsin Avenue. Photo from Wikimedia Commons.
Wisconsin Avenue. Photo from Wikimedia Commons.

It’s a solid seven-hour drive to Georgetown from Newburyport, yet when you arrive you’ll probably feel right at home. Georgetown’s got the brick walkways and water view like Newburyport and Portsmouth, and some ridiculously beautiful homes to boot. You’ll also find that it’s the stomping grounds for America’s political elite, and there’s no lack of classy restaurants and expensive boutiques to prove it.

Score points with: A canal cruise, some Ethiopian at Das Ethiopian and a heaping ice cream cone at Thomas Sweet.

5. Coastal town #5: Annapolis, Maryland


Just an hour from the District, Annapolis is the quieter version of Georgetown — same weather, same permeation of politics and national history (home to St. John’s College and the naval academy) but a more relaxed atmosphere. It’s also the first place you’ll find Kilwin’s on this tour, possibly my favorite ice cream in America.

Score points with: Crab cakes off the water, a visit to Kilwin’s for some ice cream or fudge, and a tour of the naval academy, which hosts some of the most beautiful buildings I’ve seen in a college atmosphere, ever.

6. Coastal town #6: Wilmington, North Carolina

A view of Front Street in Downtown Wilmington. Photo from
A view of Front Street in Downtown Wilmington. Photo from

Six hours south of Annapolis is Wilmington, a former home of mine and increasingly beautiful each time I brace for my current Chicago’s frigid winters. You’re definitely in the south when you hit Wilmington, and the slower pace, weeping willow-lined streets and warm people make you want to stay forever.

Score points with: Dinner on one of the balconies at the Riverboat Landing, a visit to the cute shops and art studios of the Cotton Exchange, and sunset drinks at Level 5, an outdoor rooftop bar above City Stage, Wilmington’s local theatre.

Try all of these places on a road trip, or once at a time. If you love historic towns, friendly people, and endless seafood like I do, you won’t want to miss any of them.