Hugh-K-Telleria/Shutterstock One of the original major cities of the Gold Rush, Jacksonville was founded in the early 1850s by pioneers hoping to strike it rich. The entire town, which has a population of about 2,800, was designated as a U.S. National Landmark in the 1960s, so it’s definitely worth visiting, especially if you’re a history buff. Jacksonville is home to over 100 National Historical buildings sprinkled throughout the community in the heart of Oregon’s wine country and surrounded by gorgeous greenery, so there really is something for everyone. Insider tip: Consider staying in one of the incredibly adorable family-owned bed and breakfasts or inns for an extra small-town feel. We’re told they offer exceptional service and amazing dinning options. Plus, check out the most charming small-town bed and breakfast in every state.
Traverse City, Michigan
Briana-Paige/Shutterstock Located on the shores of Lake Michigan, Traverse City is the ultimate outdoor and water activities destination. In the warmer months, you’ll find everyone hiking and biking the numerous trails and participating in the most popular recreational water sports—kayaking, fishing, windsurfing, and paddleboarding. There’s also golfing and bird watching for those who are looking for a more leisurely vacation. July is an especially busy month in Traverse City, as it’s when hundreds of thousands of visitors come in for the National Cherry Festival (the city boasts being the largest producer of tart cherries in the country). And the many farm-to-table dining options, breweries, wineries, and distilleries make it a destination worth visiting even in the winter.