21 U.S. Destinations to Visit in 2021: Ashland, Oregon

The Pacific Northwest is full of small-town escapes— the only question is, do you want to head towards the coast, the mountains, or the wine regions? The charming town of Ashland, Oregon, has been attracting performing arts lovers for decades. From February through October, the Oregon Shakespeare Festival performs approximately a dozen Shakespearean and non-Shakespeare plays, amounting to over 800 performances each season. As with most theatrical productions, the 2020 season was cancelled, but we are optimistic that 2021 will be different and the theatregoers will be back to check into the boutique hotels, walk through Lithia Park, and enjoy the culinary scene before showtime at one of the three venues. For anyone that enjoys live performances during their travels, this is a bucket list item!

Between performances, the walkable downtown includes bakeries, coffee shops, cafés, and restaurants, as well as two breweries and a distillery. Just outside downtown you will find a nice selection of Rogue Valley wineries — there’s no shortage of award-winning wines to taste. Add some excitement and adventure to the trip and book a half-day or full-day rafting excursion on the wild and scenic Rogue River.

Plan to stay for a few days— there are a few hidden gems to explore in the surrounding towns. The former gold rush boomtown of Jacksonville has an impressive food and wine scene and live music being played at many spots across the historic downtown. If you ask the locals what to do, there’s a good chance they’ll tell you to visit Central Point, specifically for handmade cheese at Rogue River Creamery and chocolates at Lillie Belle Farms. Nearby is also one of the last bespoke hatters in the country— step into VS Custom Hats and try on some of the men’s and ladies’ dress and Western styles.

**Due to the COVID-19 pandemic, many states have travel restrictions and attractions may be temporarily closed or have limited hours. We direct you to their websites for updates and add them to your list for future travels!