Cape Cod comprises dozens of small towns with wood-shingled houses that turn gray with the salt air, but none are as popular as Chatham. With a population of 6,125, this charming little town has two beautiful resorts with water views, and fine dining caters to the area.
The high-end stores lining its “downtown” are mere steps from the ocean, where on any given day, you will see the herd of seals that call this area home.
Oregon: Hood River
Hood River is a peaceful gateway into some of the state’s best nature, chock-full of scenic hiking and mountain biking trails, craft breweries, wineries, and farm-to-table bounty.
With a population of 7,688, this town is overlooked by the Columbia River Gorge, meaning you can engage in several outdoor activities that include hiking, skiing, paddle boarding, and mountain biking. The 1886 E.L. Smith Building is the oldest in the city.
The "Best Little Town" in the state has a population of 400 who enjoy incredible views of Devils Tower, which is America's first National Monument. However, that population balloons to over 100,000, with bikers en route to the annual Sturgis Motorcycle Rally in South Dakota.
Whether you decide to explore the area on a motorcycle or horseback, you'll want to make time on your schedule for a meal at the Ponderosa Cafe, a place that fits the town's Old West vibe.
Missouri, Sainte Genevieve
As this town's name suggests, Sainte Genevieve was originally a French Canadian town, and history is one of its major draws. Laying claim as the oldest town in Missouri, it lauds an impressive historical museum and buildings dating back 200 years.
Some of the Sainte Genevieve homes are superbly preserved, while others lay abandoned and ramshackle, providing an eerie atmosphere that's equally compelling.
With a population of 2,494, this former silver-mining town sits near a dead-end valley, with mountains sporting gorgeous waterfalls: Telluride's Bridal Veil. With peaks great for mountain biking, skiing, or hiking. Telluride may be the most walker-friendly ski town in North America.
This town has blossomed into one of the nation's best festival sites, with renowned events like the Bluegrass Festival and Telluride Film Festival.