Road Tripping the Oregon Trail

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Oregon offers many travel opportunities for active baby boomers. Sheri Wallace, editor of  Road Trips for Families, says,”The Mt. Hood region of Oregon has compelling history, spectacular scenery, every outdoor activity imaginable and, unlike the pioneer’s Oregon Trail, is easy to road trip.”  In today’s guest post, Sheri offers her advice to baby boomers considering a visit.

Mt Hood

The area surrounding Mt. Hood, Oregon, to the south and east of Portland, is one of the most scenic in the U.S. This area is home to the culmination of many a pioneer’s dreams — Oregon City and the last stop on the Oregon Trail. In many places, the road you’re traveling is close to the original trail.

Unlike some destinations, there is no season when activities cease or when the scenery is less spectacular. Winter and spring bring snow sports to the top of recreation lists, but there are still other alternatives if you stay in the lower elevations. Spring, summer and fall are packed with agritourism offerings, including farm tours, u-pick fruit and produce stops plus lots of outdoor recreation options. Mt. Hood itself has something for everyone. Whether you prefer the scenic drive with minimal activities or enjoy hiking or even snowmobiling or geocaching with the grandkids, you’ll find something for every experience and fitness level.

Hit the Trail

This Oregon road trip is particularly appealing because it can be done in less than 100 highway miles, so there are no long stretches in the car to plan for. Whether you spend a weekend or a week, it’s easy to just roam from place to place and not feel rushed. Unlike the real Oregon Trail, the road trip is easy and fun, and great for grandkids. Start your trip with a visit to the Mt. Hood Territory web site for information on events and festivals and to order a travel planner for the region.

Before you go, read a book or two about the trail and bring a historic site guide along on the road trip.

Not exactly part of Oregon Trail history, but fun for history buffs nonetheless, The Bomber Restaurant, in Milwaukie is home to one of only 11 intact B-17G bomber planes in the world. The restaurant has several hours worth of reading material and interesting stories about the plane. Food is diner style, and very popular with the locals.

Tour the Sandy Farm Loop on the way to Mt. Hood. Mostly agritoursim stops, there are about 20 different farms and stores along the route selling fresh produce, flowers, honey, fruits and more. Kids will love the alpacas! If you’re interested in gardening, be sure to stop at Red Pig Garden Tools & Blacksmith. They offer the largest variety of manual gardening tools in the US, many forged by blacksmith Bob right there at the farm. After the loop, stop at Joe’s Donuts for a sweet snack and take a tour of the Sandy Historical Museum. Located on Barlow Road, the museum has an extensive photo gallery and exhibits from pioneer and the logging industry.

Adventures on Mt. Hood

Timberline Lodge

When traveling, it’s wise to keep in mind that a passable way around Mt. Hood took years to build. Conditions on the roads can change rapidly, so use TripCheck to get up to the minute road conditions and weather advisories, especially in winter.

Mt. Hood Adventure specializes in outdoor recreation on Mt. Hood. Call before you travel and arrange for activities with their experienced guides. From bird watching to adventure sports like snowboarding, they’ll make sure you have a great time.

Visit Timberline Lodge if weather permits. The view is stunning and the ride up the mountain is half the run. The self tour of the lodge has a lot of history, included at the very budget-friendly cost of free, and the fireside brunch is highly recommended. Also be sure to stop at the Wildwood Recreation Site, the Mt. Hood Cultural Museum and investigate taking a class at the Arts Cabins Project.

Enjoy the Region

Ladybug Chocolates

After spending some time on the mountain, take at least a day and tour the eastern part of the county. The Canby Historical Society Depot Museum is housed in Oregon’s oldest railroad station. Baby boomer chocolate lovers will enjoy stopping at Ladybug Chocolates and Puddin River Chocolates for some snacks to take on your ride on the Canby Ferry.

This part of Oregon is world renowned for wine, so make a pit stop at St. Josef’s Winery for a tasting. The winery is also a fantastic place to have a picnic or take photographs. Make sure to ask about the history of the buildings and the family’s wine-making experiences. Another option is the AlexEli Winery.

If You Go:
Casa de Tamales
, Milwaukie:  Famous for their 40 different tamales and asparagus mole, tamale and fried asparagus. Definitely worth the drive!
Highland Still House & Pub:  Portland’s largest selection of single malt scotch, wide selection of local, Irish and Scottish beers in authentic pub environment.
Gustav’s:  German food and beer with fresh, northwest ingredients. Several locations.
Ice Axe Grill: Mt. Hood Brewing
Charlie’s Mountain View
Rendezvous Grill & Tap Room
Still Creek Inn & Lounge

Courtyard Portland Southeast
Mt. Hood Vacation Rentals
Mt. Hood Village RV Resort
Marriott Fairfield Inn and Suites, Lake Oswego
Crowne Plaza, Lake Oswego

All photos provided by Sheri Wallace.

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