Winter Park, FL--outside of Orlando. In a metro area that is otherwise mostly categorized by theme parks, urban sprawl, and cookie cutter master planned "developments", Winter Park is such a gem! Gorgeous old homes set among palm trees, lakes, beautiful college, cafes, independent shops. Lovely area.

Marquette Michigan in the Upper Peninsula...gorgeous natural scenery and a liberal, outdoorsy vibe

Not really a town but the whole Black Hills area in South Dakota is so underrated. It's beautiful and there is so much to do!

Floyd, VA. It has quite the little artsy, hippie vibe! And a general store that hosts flat footing on Saturday nights, which makes you feel like you've gone back in time if you experience it (not in a bad way).

Staunton, VA is really cute, went to college there for a bit before transferring.

Portsmouth, NH
Spent 4 days there for work and was utterly charmed.

Anonymous wrote:There was a town in central Massachusetts, when I was driving from my family in the Berkshires to my family in Boston, that was a delight. The stop was quick, and it was raining heavily, but I stopped into a cute hippie grocery and got yummy soup, there were so many nice little bookshops, and there was a bridge covered in flowers! I forget the name but it was a real gem of a town.

Shelburne has the bridge with flowers. Lots of great towns near there in Franklin and Hampshire counties!

There was a town in central Massachusetts, when I was driving from my family in the Berkshires to my family in Boston, that was a delight. The stop was quick, and it was raining heavily, but I stopped into a cute hippie grocery and got yummy soup, there were so many nice little bookshops, and there was a bridge covered in flowers! I forget the name but it was a real gem of a town.

Anonymous wrote:Rochester, NH

Wild Willy's burgers and fries!

We bought a dog from a breeder here. I was unaware it was the hometown of slain photojournalist James Foley until we ate at Wild Willy's and his photo was hanging on a bulletin board there.

Corning, NY

Skaneateles, NY--I didn't love Syracuse so this was a pleasantly surprising side trip! Also Collingswood/Pennsauken/Cherry Hill area of NJ right outside of Philadelphia...I liked walking around Cooper River Lake and we had some good meals there.

And while they are cities and not towns, my spouse and I both had our expectations exceeded in Omaha, San Antonio, and Oklahoma City.

Lincoln, Nebraska

Custer, SD. I had the best veggie burger I ever ate there!

Everwood, CO. Bluebell, AL.

Fernandina Beach

Rochester, NH

Farmland, Indiana. It has one stoplight. It has a malt shop, an antique store, a tiny coffee company, and a glass blower/stained glass window studio. It’s about an hour north of Indianapolis, and I never would have known about it if friends didn’t have a lake house nearby. It reminded me of Schitt’s Creek—in a good way!