A Tour Of American History
If you love walkable downtowns, coastal views, and that crisp, mid-to-northern vibe where a good jacket is part of the plan, the upper half of the East Coast is calling. This stretch packs in colonial history, artsy neighborhoods, waterfront food scenes, and cities that feel alive without always feeling chaotic. You’ll get everything from big-name icons to smaller gems that still know how to surprise you.
1. Portland, Maine
Portland greets you with salty air, brick streets, and a food scene that’s way better than a city this size has any right to be. The Old Port is perfect for wandering, especially when you’re popping into bookstores and grabbing seafood that tastes as if it came straight off a boat. If you’ve got time, take a quick ride out into Casco Bay and let the ocean breeze wash over you.
2. Bar Harbor, Maine
Bar Harbor feels like a postcard that sprung to life, with harbor views and a lingering scent of pine. It’s the classic basecamp for Acadia National Park, so you can go from coffee to mountain-and-ocean scenery in no time. Evenings here are made for slow walks and fresh seafood.
Michael & Diane Weidner on Unsplash
3. Burlington, Vermont
Burlington mixes lake views with a laid-back, outdoorsy energy that makes you want to stay longer than planned. You can stroll the waterfront on Lake Champlain, then head downtown for live music and local eats. Even with the more relaxed vibe this city brings, you’ll still find plenty to do.
4. Stowe, Vermont
Stowe is small, but it punches above its weight when it comes to scenery and charm. In the fall, the colors feel unreal, and in the winter, it turns into a skiing paradise. If you like your trips to include nature exploration and a warm place to refuel afterward, Stowe fits perfectly.
5. Portsmouth, New Hampshire
Portsmouth has historic streets, a gorgeous waterfront, and a downtown that practically begs you to linger. You can grab a nice meal, browse shops, and still make it to the water in minutes. It’s charming, without being sleepy.
6. Boston, Massachusetts
Boston gives you history, culture, and a strong sense that the city has opinions about everything, including where you should eat. Walk the Freedom Trail, then veer off into neighborhoods where the best moments are the unexpected ones. By the time you’ve taken a harbor stroll and found a cozy pub, you’ll get why people stay loyal to this city.
7. Salem, Massachusetts
Salem leans into its spooky reputation, but it’s also a genuinely fun coastal town with museums, shops, and harbor views. You can do the witch-history deep dive if you want, or just enjoy the walkable streets and seaside energy. Visit outside peak October crowds, and you’ll get a much calmer, more charming experience.
8. Providence, Rhode Island
Providence has a creative streak that shows up everywhere, especially in its food and arts scenes. If you catch WaterFire, the city glows in a way that feels both dreamy and a little surreal. It’s an easy weekend city because everything you want is close together, and you’re never far from your next good meal.
9. Newport, Rhode Island
Newport is where you go when you want ocean views with a side of old-school glam. The city is full of Gilded Age architecture, yachts, and musical history. Plan your trip around its annual jazz or folk festival, or enjoy a walk down its beautiful coast.
10. New Haven, Connecticut
New Haven is smart, lively, and unapologetically proud of its pizza scene. Yale’s museums and architecture make the city feel scenic and cultured. Come hungry, though, because the best way to understand New Haven is one slice at a time.
11. Mystic, Connecticut
Mystic is cozy, coastal, and built for slow wandering with a coffee in hand. The historic seaport and waterfront areas give it that classic New England charm you’re looking for, but without feeling bored. If you like boats, chowder, and cute shops, you’ll feel right at home.
12. New York City, New York
New York City is a whole world, and even a short visit feels like you’ve lived three different days at once. You can do museums and landmarks, but the best moments often come from wandering a neighborhood and following your curiosity. Permit yourself to do less, because the city will still deliver.
13. Hudson, New York
Hudson feels like a small city with big taste, full of antiques, galleries, and excellent food. It’s a great stop if you want something artsy and slower-paced without feeling bored. Pair it with a scenic drive through the Hudson Valley, and you’ve got an easy win of a weekend.
14. Albany, New York
Albany doesn’t always make flashy travel lists, which is exactly why it can be a good surprise. The architecture, museums, and riverfront areas give you a solid day of exploring without the tourist crush. It’s also a handy jumping-off point for the Adirondacks if you’re craving more nature.
15. Philadelphia, Pennsylvania
Philadelphia is one of those cities where you can do iconic history and then immediately eat something incredible. Old City is perfect for wandering, and the museums are the kind you actually want to spend time in. By the end of the day, you’ll realize just how much personality the city really has.
16. Pittsburgh, Pennsylvania
Pittsburgh sits a bit inland, but it’s a northern gem with serious skyline views and a creative, friendly vibe. Ride the Duquesne Incline for that “wow” moment, then explore neighborhoods full of murals, breweries, and great food
Vidar Nordli-Mathisen on Unsplash
17. Jersey City, New Jersey
Jersey City gives you skyline views of Manhattan without the constant crowds. The waterfront is great for walks, and the food scene is quietly excellent. If you want big-city access with an option to escape if need be, this is a smart pick.
18. Newark, New Jersey
Newark is a practical, underrated stop with easy transit connections and a growing arts and food scene. You can catch a show at the New Jersey Performing Arts Center and then explore local spots that feel distinctly Jersey. It’s not trying to be charming, but it still has plenty going for it.
19. Baltimore, Maryland
Baltimore has grit, heart, and neighborhoods that feel like their own little worlds. The Inner Harbor is the obvious start, but the best parts often show up when you branch out to places like Fells Point or Hampden. Come with an open mind, and you’ll leave with a soft spot for it.
20. Washington, DC
Washington, DC, is packed with museums and monuments, but it’s also a great city for long walks and great meals. The Smithsonian spots can take days, and many of the best ones are free, which feels like a small miracle. When you’re ready to relax, find a neighborhood café and enjoy how unexpectedly livable the city feels.
