# @cnntravel on Instagram

- **Type:** Image
- **Original URL:** https://www.instagram.com/p/DMikHjevK6w
- **Gondola URL:** https://gondola.cc/posts/32681239-cnntravel-instagram
- **Thumbnail:** https://img.gondola.cc/tr:w-,h-,fo-auto/postThumbnails/d71909a462.jpg
- **Posted:** 2025-07-25T18:01:16.000+00:00
- **Account Owner:** CNN Travel (@CNNTravel) — https://gondola.cc/CNNTravel

## Caption

It's Sunday night at Middleton Tavern, where a handful of drinkers at the rustic wooden bar are surrounded by glimpses of America's colonial past.

Copper pots hang over a fireplace, while seascape paintings, farm tools, old naval uniforms and models of sailing ships adorn the walls. The patio offers views of Annapolis' City Dock, where Chesapeake Bay watermen once brought in the day's catch.

And the tavern itself dates to 1750 – before America became a country – when Horatio Middleton opened it to lodge travelers crossing the bay on his ferry. If you believe the local lore, George Washington and Benjamin Franklin once drank here.

"This is one of the oldest – if not the oldest – bars in Maryland," says bartender Steve Frederick, an amiable guy with a lanky frame and a trucker hat. "There's a lot of history here."

Indeed, there's a lot of history throughout this cozy waterfront city, whose narrow streets, brick sidewalks and handsome Georgian buildings could serve as an 18th-century movie set.

But Annapolis, Maryland's capital and a 45-minute drive from Washington, D.C., offers visitors much more than historic charm. A key port on the Chesapeake, it provides numerous ways to explore the Bay, from sunset cruises to outings aboard a historic skipjack, a working sailboat once used for dredging oysters. All this and more lands it at No. 5 on CNN's list of America's Best Towns to Visit for 2025. Swipe to explore some of its best spots, and read more at the link in our bio.

#annapolis #annapolismd #annapolismaryland #annapolisphotographer #annapolislife #maryland #marylandphotographer #marylandlife

📸 Rebecca Wright/CNN

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## Tags

annapolis, maryland, marylandphotographer, annapolismaryland, marylandlife, annapolisphotographer, annapolismd, annapolislife

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