Join us for the 14th annual Oakland Sip & Stroll! Celebrate the city of Oakland and surrounding counties.

Saturday, November 23, 2019 -Sip & Stroll: 12:00pm - 5:00pm 

Each participating business will have a winery or brewery and local foods to sample.

Go on the treasure hunt to get your passport stamped by businesses hosting our participating wineries and breweries. Completed passports will be entered to win one of many great gift baskets.

The core of downtown Oakland's historic district will be closed to all but emergency traffic allowing participants to visit the businesses and the vendors.

Rides in the Cinderella horse drawn carriage will be available for purchase, $10 for adults and $5 for children 12 and under.

Enjoy the pre-holiday season where you can purchase your gifts while enjoying food and beverage.

Passports are $15 and include a tasting glass. 

After Party: 5:00pm - 7:00pm

Once your passport is completed, turn it in and join us at one or all of the following locations for our progressive giveaway! You must be present to win.

Food and drink will be available for purchase.

5:00pm - The Speakeasy

5:30pm - Tolly's

6:00pm - Triple Oak Wine Vault

6:30pm - 1918 Speedshop


  • Occurred Saturday, November 23rd, 2019 @ 12:00 pm – 5:00 pm


Downtown Historic Oakland

100 Locust St.
Oakland, OR 97462


Michele Everett