October 16-19, 2025
October 16-19, 2025
Sunshine and Summer Jams
Jump into summer in Ashland with these fun themed ideas and things to do. We have you covered whether it’s a family road trip or a romantic retreat. There is no shortage of adventures with something for everyone.
Sunshine and Summer Jams
Welcome to one of the Top 5 Wine Regions in the World
Ashland’s wine and culinary scene invites you to get away for the weekend and taste the flavors. The holidays make a perfect time to visit our tasting rooms and discover a new varietal. As the gateway to Rogue Valley Wine Country, Ashland is home to 7 amazing wineries and that is just the beginning. Rogue Valley AVA is one of the Top 5 Wine Regions in the World according to Wine Enthusiast.
Welcome to one of the Top 5 Wine Regions in the World
Ashland’s wine and culinary scene invites you to get away for the weekend and taste the flavors at over 100 restaurants. Start your journey here in Ashland to discover a new, favorite varietal at one of Southern Oregon’s award-winning wineries and that is just the beginning. Rogue Valley AVA is one of the Top 5 Wine Regions in the World according to Wine Enthusiast.
Feel big city culture in a modern mountain town
We proudly offer 365 days of theatre, art, music and fun. Plan your trip today to enjoy theater this winter. Our retailers are ready to welcome you with a unique shopping experience. Meet musicians and artists who love sharing their amazing creativity. Make plans now to join us for OSF's 90th season coming this March, with 9 plays in repertoire, there is a seat waiting for you! Come feel the culture here.
Feel big city culture in a modern mountain town
There is a seat waiting for you at a theatre in Ashland. Our retailers are ready to welcome you with a unique shopping experience. Meet musicians and artists who love sharing their amazing creativity. A spectrum of culture awaits
Stay with us
Come experience homegrown hospitality. Whether traveling with friends, the entire family, on a solo bike trip or a holiday getaway, Ashland offers something for everyone. From local food and wine to unique B&Bs, Ashland’s hospitality is steeped in the area’s rich culture, landscape, and history.
Stay with us
Enjoy the coziness of the season together when you stay in Ashland. Whether downtown or tucked away in the mountains, Ashland offers something for everyone. From local food and wine to unique B&Bs, Ashland’s hospitality is steeped in the area’s rich culture, landscape, and history.
Unplug to reconnect
Relax and refresh at one of Ashland’s spas or soak up the fresh air on the trails that meander through the Ashland Watershed. From the tranquility of Lithia Park to the delicious flavors our chefs create, you are invited to come and unwind.
Pamper yourself in local magic
Relax and refresh at one of Ashland’s spas or soak up the sunshine on the trails that meander through the Ashland Watershed. From the tranquility of Lithia Park to the delicious flavors our chefs create, you are invited to come and unwind.