13th Annual Sip & Stroll in Historic Oakland Oregon


Stroll, Sip and Shop in Historic Oakland at the13th annual Sip & Stroll, Sunday, November 18th from 12 pm to 4:00 p.m. YES, the name has been shortened and includes Wine and Beer.

Enjoy a relaxed late autumn Sunday afternoon (rain or shine) as we get ready for Thanksgiving and the Christmas shopping season. Enjoy music performed by the strolling Oakland Singers dressed in period attire.

This year, the streets will be closed with added vendors throughout town!

Participating Oakland shops will open their doors to Umpqua Valley wineries and breweries for your tasting pleasure. Unique works by local artists as well as a variety of fine gifts and antiques for sale at the many shops throughout downtown. Get your passport stamped at each participating shop for a chance to win great prizes.

Purchase your passport and tasting glass for just $10 (no purchase required to participate)

Must be 21 or older

Complete and turn in by 3:45 pm for drawing at 4:00 p.m (must be present to win)


  • Occurs Sunday, November 18th, 2018 @ 12:00 pm – 4:00 pm



Linda West

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