10/26/2026
Fall looks good on Ashland. 🍂 Leaves all over Lithia Park, sweater weather, and plenty of reasons to make a weekend of it. Bring the kids or plan a few nights away together, here are five dates to put on your calendar:
🎶 RoxyAnn Halloween Party | October 30
RoxyAnn W**ery, 3283 Hillcrest Road, Medford
Live music from The Pozitronics, a costume contest, BBQ, and local w**e make a fun evening out.
RoxyAnn W**ery
🎃 Children’s Halloween Celebration | October 31
Downtown Ashland, starting at Gresham & East Main
Join the costume procession at 3:45 p.m., followed by music and trick-or-treating at downtown businesses.
Ashland Chamber of Commerce
🍷 First Friday with Calysta Cheyenne | November 6
Resistance W**e Co., 322 North Pioneer Street, Ashland
Make a date of live music, wood-fired pizza, and Rogue Valley w**e from 6–8 p.m.
Resistance W**e Company
✨ Festival of Light Kickoff | November 27
Downtown Ashland Plaza
Festivities begin at 3 p.m., with Santa’s Parade and the Grand Illumination welcoming the holiday season.
Ashland Chamber of Commerce
Pick your weekend, pack an extra sweater, and come stay with us at Swank House. We’d love to have you.
TravelOregon