Refuel with a sweet treat, a pint of craft beer or a full meal at Tolly's Grill & Soda Fountain in Oakland.

Take a detour off of I-5 near Roseburg, and you’ll feel like you’ve stepped back in time in the town of Oakland. Just 16 miles north of Roseburg and a stone’s throw off the interstate, this charming little burg of 927 souls preserves the roots of Oregon’s pioneering settlers and wine industry.

The first town to make Oregon’s historic register, Oakland offers a tour through 19th-century architecture. View Victorian-era homes and scores of other historic storefronts built in the 1800s on a self-guided tour. Stop in at the Oakland Museum for a closer look at the town’s past. Don’t miss the Rochester covered bridge, one of only 50 in Oregon.

Antique lovers can browse through history at a variety of shops, including Oakland Antiques, Oakland Trader, Olde Town Antiques and Page and Dimmick Antiques. Many of the shops are housed in beautiful 19th-century buildings.

Take a tour of Oakland’s wineries, which include MarshAnne Landing, Misty Oaks Vineyard, Sienna Ridge Estate and Triple Oak Vineyard. These and others in the region make up the Umpqua Valley AVA, which has nearly two dozen members and is the oldest wine region in Oregon.

When it’s time to refuel, The Hollow Coffeehouse has you covered for coffee, pastries and breakfast sandwiches. Stop at the old-fashioned ice cream parlor, Tolly’s Grill & Soda Fountain, for a sweet treat, a pint of craft beer or a full meal.

about author Eileen Garvin

Eileen Garvin lives and writes in Hood River. When she’s not hunched over her keyboard or digging in the garden, you can find her mountain biking, kiteboarding, hiking, skiing or camping somewhere in Oregon.

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These maps and directions are for planning purposes only. You may find that construction projects, traffic, or other events may cause road conditions to differ from the map results. For travel options, weather and road conditions, visit tripcheck.com, call 511 (in Oregon only), 800.977.6368 or 503.588.2941.

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  1. Nancy says…

    We took this little side trip last week on our trip to Ashland. It was everything promised and then some. We found the town of Oakland charming and very friendly, excellent breakfast at Trollys and a great cup of coffee at the Coffee Hollow. We then went on to the Rochester Covered Bridge. Thank you for this article as I would never have known about Oakland!

    Written on May 15th, 2013 / Flag this Comment
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