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Annual Halloween Promenade in Downtown Jacksonville

Annual Halloween Promenade in Downtown Jacksonville is on Sunday, October 25, 2026 from 12:00 PM to 3:00 PM at downtown jacksonville in Medford, OR. Free to attend.

When

Sunday, October 25, 2026, 12:00 PM – 3:00 PM

Where

downtown jacksonville

Cost

Free

Downtown becomes a kid-friendly Halloween stroll with costumes and trick-or-treating at participating businesses.

Also on Sunday

• 10:00 AM – 5:00 PM Lithia Artisans MarketCalle Guanajuato · Behind the Plaza, Ashland

  50+ local artisans along Ashland Creek: jewelry, pottery, woodwork, clothing and art.
• Spotlight 11:00 AM – 3:00 PM Medford Railroad Park Run DayMedford Railroad Park · 799 Berrydale Ave

  Last run day of the season: ride the miniature trains and tour the model railroad layouts. Free; donations welcome.
• 11:00 AM – 1:00 PM SunFolk Dancing at The GrangeAshland Bellview Grange · 1050 Tolman Creek Road, Ashland

  Eastern European folk dancing to live music! No experience necessary. No partners needed. Sundays at Bellview Grange. 1050 Tolman Creek Rd. Ashland, OR 97520
• 12:00 PM – 4:15 PM Beginner Dungeons & Dragons, 8-12 YRSMeeting Room, Eagle Point Library

  Introductory Dungeons & Dragons sessions for ages 8–12; materials provided and newcomers are welcome.
• 12:00 PM – 6:30 PM Jacksonville Wine TrolleyJacksonville-area wineries · Downtown Jacksonville

  Hop-on, hop-off trolley between Jacksonville-area tasting rooms. $30 day pass, $45 three-day, $15 happy-hour pass after 3 PM.
• Spotlight 7:30 PM (doors 7:00 PM) Lyle Lovett & His Small Large BandThe Holly Theatre · 226 W 6th St

  The Texas songwriter and his big band at Medford's restored 1930 movie palace. $79 to $115.

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