Winterset, which is located in Madison County, Iowa, is known for its covered bridges. It’s been used as a shooting location for several films, including The Bridges of Madison County, in 1995, and The Crazies in 2010. The town even hosts a Covered Bridge Festival each year during the second week of October.
Aside from visiting the bridges, try heading to the house where John Wayne was born, which has been converted into a museum. And, of course, if you’re looking for a place to stay, the Covered Bridge Inn may have a room for you!
Vermont: Stowe
This charming resort town is known for its natural beauty and great ski trails. During the warmer seasons, visitors can hike, bike, and climb their way through areas like Moss Glen Falls or Sunset Rock Trail. If you hike the trails at Smuggler’s Notch State Park, you’ll be able to see the Bingham Falls swimming hole. It gets pretty crowded during the summer weekends, so make sure to plan ahead!
There are plenty of great places to stay in and near Stowe, but if you’re in town for the skiing, you’ll definitely want to check into the Topnotch Resort and Spa for incredible mountain views and cozy accommodations. No matter what time of year you go, you’re in for a real treat!
Maine: Kennebunkport
Maine has quite a few small towns worth visiting, many of which offer gorgeous views of the Atlantic, and some of the best lobster you’ve ever eaten in your life. One town, however, stands out among the others. Kennebunkport, which likes to refer to itself as “the place to be all year,” is a resort town full of beautiful beaches and fun things to do.
The town is also home to the Bush family summer home, Walker’s Point Estate, where the former president and his family spend a lot of time on vacations. The gates to the estate are guarded by the Secret Service, though you can catch a glimpse if you happen to rent a boat and cruise by.
Michigan: Charlevoix
Charlevoix is a gorgeous resort town right on the lake in Northern Michigan. Anyone who’s been knows that driving over the hill into town makes you feel as though a weight has been lifted off your shoulders, and you’re driving into paradise. There’s something to do any time of year. During the summer, walking along the waterfront or boating through the harbor. During the winter, the area boasts some great skiing.
If you’re on the hunt for luxury lodging with amazing views, check into the Inn at Bay Harbor for an amazing sunset viewing right from your balcony. Make sure to head to Smoke on the Water for breakfast or brunch one morning, too. If you like eggs benedict, they’re very highly recommended.
Massachusetts: Edgartown
This little town in New England is located on the island of Martha’s Vineyard. It’s known for being one of the most beautiful communities in the state, and area in general. Full of beautiful beaches and vacation homes, it’s frequented by high-profile figures, including the late Princess Diana, former president Barack Obama and his family, and comedian/talk show host, David Letterman.
Take the Edgartown tour and hit all of the lighthouses for some spectacular views. If you happen to be in town in June, be sure to stop in for the Taste of the Vineyard festival, where you can enjoy all of the culinary delights (and wine) that the town has to offer.