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 - Triple Oak Wine Vault

6:00pm - 1918 Speedshop

Check us out on Facebook, Instagram, and our website for updates.




Admission: $15.00





Lodging available at Motel 6 Sutherlin & Roseburg! Event special at $65/night. Call hotel and use the code OSS2019.

Roseburg - 541.464.8000

Sutherlin - 541.459.6800

Best Western Hartford Lodge

150 Myrtle St.
Sutherlin, OR 97479
Ph: (541)459-1424
Call the hotel and ask for Sip & Stroll Discount (15%) off of best available price.

Great Northern Trailer Works will be offering shuttle service from both Motel 6 & Best Western in Sutherlin!

11:30am - 12:30pm, 5:00pm - 7:00pm, 9:30pm - 10:15pm

Local Businesses

Bart's Market

Pepper & Company

1918 Speed Shop

The Historic Oakland Tavern

Oakland Flour Mill

Sandwich Shop - Opening Soon

Beautiful Emporium

Lotus Yoga

Lamplighter Inn

1905 Emporium – Oakland Ice House

CoCo’s Restaurant

Page & Dimmick Building

Triple Oak Wine Vault

CoCo’s Restaurant

The Speakeasy