You may Live and Breathe letterboxing but every now and again it’s a good idea to come up for air. Luckily, Oregon offers ample opportunity for you to Take a Break. Wait! Isn’t that the name of a letterbox? The state of Oregon has an incredible range of diversity, from the 11,239 foot summit of Mount Hood, to the sagebrush desert, to the dense evergreen forests of the Cascades, to the shores of the Pacific Ocean. Even more luckily, every part of the state is home to letterboxes. You can take in the sights AND snag some hidden treasures. Hopefully, you will have a wee bit of extra time to take in some of these special places.

The City
Let’s begin your tour in the largest city in the state, Portland. There are a few must-see letterboxes to be found. The Spirit of Dartmoor is a classic, one of the first boxes in the country. Sharpen your pencil and figure this one out. Jay’s Toolbox is an innovator, possibly the first add-on box in the country. Bring a tiny tool stamp to add to Jay’s stash. The Musician Series hosts an ever-expanding gallery of stamp art by carvers from many states. Please consider adding an artist of your own to this collection hidden along a flat forest trail in Forest Park. This park bills itself as the largest natural urban forest in America, complete with stands of old growth. With over seventy miles of developed trails, it’s naturally home to scores of letterboxes. For good, free maps check out this website.

Washington Park, adjacent to the city center, at the southern end of Forest Park, is home to the test gardens for the International Rose Society, the Oregon Zoo, the Hoyt Arboretum, the Children’s Museum, the Vietnam Memorial, the Forestry Center, the Holocaust Memorial and my personal favorite, the amazing musical fountain. Even many locals don’t know about The Chiming Fountain, found near the east entrance to the park, off SW Washington Street. Step inside its lower wall, stand beneath the upper bowl and listen to the notes chimed by the falling waters. From this spot, you can see a lovely bronze statue of Sacajawea, the first public sculpture in the US created by a woman. Susan B. Anthony visited Portland for the dedication ceremonies. Keep in mind that letterboxes abound all around you at this point. For more maps and info go here.


The entire downtown area is served by the free electric Max train. Outside of the “fareless square” area you will have to buy a ticket but the underground station at the Oregon Zoo is well worth the fare for you geology buffs. At 260 feet below ground it is the deepest train station in North America and has a wonderful display of a core sample extracted during construction which has the different geological eras marked on it.


No trip to Portland would be complete without a visit to Powell’s City of Books, the largest independent used and new bookstore in the entire world! The flagship store is at the corner of SW 10th and Burnside and includes a coffee shop, if you are in need of refreshment. This place is so huge that you need a map, available at the entrance, to find your way around.


If your refreshment needs are more substantial there are a couple of historic favorites to visit nearby. For over a century Dan and Louis Oyster Bar has been feeding Northwest families, celebrities and visitors from a far. Another classic dining spot is Portland’s oldest restaurant, Hubers, a few blocks south. This restaurant is famed for its hand-carved turkey as well as the theatrical presentation of its decidedly adult treat, a flaming Spanish coffee.

The entire strip along NW 23rd Avenue is filled with interesting places to eat and spend your hard earned cash in small trendy places of business. If you’re shopping for outdoor gear, REI’s downtown branch has a hugh selection. If you are in need of art supplies, including carving media and tools, try Art Media in downtown or Columbia Art on the other side of the river.

On the east side of the Willamette River, there are also memorable spots to visit. Beneath the Hawthorne Bridge you can tour a real submarine and take in an IMAX film at OMSI, the Oregon Museum of Science and Industry.

Those with even a passing interest in skateboarding would enjoy a visit to the pioneering skatepark under the east end of the Burnside Bridge. This began as a renegade project built by local skaters and was later officially sanctioned. It’s not exactly the cleanest spot in the city but can certainly be one of the most exciting on a good day.

If you are looking for food on this side of the river, go east on Sandy Blvd. Try the hearty hofbrau fare at Gustav’s, 5035 NE Sandy, or authentic Vietnamese at any one of the dozens of restaurants along this long road. Stop for a microbrew and pizza at Laurelwood just off Sandy at 728 NE 40th. The McMenamin brothers have made a career of purchasing often derelict historic properties, restoring them and filling them with original artworks from mosaics to murals. Several of their properties have reasonable and unique accommodations in addition to family restaurants, movie theaters and pubs featuring their own microbrews and wines. Touring the grounds of Edgefield, east of the city in Troutdale, makes a worthwhile stop (not to mention letterboxes to be found.)


The Gorge

No visitor to the Pacific Northwest should miss the opportunity to see the stunning Columbia River Gorge. If you have a hankerin’ to visit neighboring Washington State, drive along Highway 14 on the north side of the Columbia River to Beacon Rock, about 45 minutes east. Take the steep but thankfully short hike to the top, snagging letterboxes along the way and views aplenty from the top. I’ve even looked down on soaring hawks from this vantage point. You can continue east from this park to The Bridge of the Gods, crossing back into Oregon. Beneath the bridge is an Oregon favorite, Charburger restaurant, for classic American fare. The walls are covered with western cowboy and Indian memorabilia. Since September is wild huckleberry season here, you will be bound to find a slice of pie stuffed with this PNW treat. Psssst... there’s a letterbox nearby!

The stretch of highway between Cascade Locks and Portland boasts some of the most beautiful scenery in the state. If you are a waterfall lover, you are in for a special treat. Get off that interstate 84 and drive the historic scenic highway. There are letterboxes at almost every fall, including the notorious Der Mad Stamper box at Multnomah Falls. This one has been considered a rite of passage by often baffled local boxers. Can you find it? Walk the trail from Horsetail to Triple Falls for the unique experience of walking behind a torrential cascade. Stop for food-with-a-view at the lovely CCC era Multnomah Falls Lodge.


Over the Mountain

Wy’east, the Multnomah Indian name for Mount Hood, looms to the south of the the mighty Columbia River, an hour’s drive east of Portland. When folks traveled the Oregon Trail in covered wagons, they came to a fork in the road along the Columbia at The Dalles, OR. Today, dams have transformed the river into a wide, smooth flow but back then travelers had to choose between rafting the river with its treacherous cascades and rapids or climbing a route via the Barlow Road with it’s terrifying Laurel Hill section. Heading east on Highway 26 from Portland. Consider stopping in Welches for a great meal at the Rendezvous Grill near mile marker 40.

Further along, you can stop at the historical marker just before mile marker 51 for a short hike to see the dreadfully steep portion of the Barlow Road where pioneers lowered their unhitched wagons by chaining them to the adjacent trees and winching them backwards downhill. At the top of the chute, you can still see deep wagon ruts. Near the rocky bottom you just might find a letterbox.

After stretching your legs here, continue east past the town of Government Camp, where you can find some good food at the Huckleberry Inn and then on to the turnoff for Timberline Lodge. Up, up, up the road you go to see an architectural treasure built by the WPA during The Great Depression.

If it’s a clear day at the Lodge, you will see other volcanoes in the Cascades chain and have stunning views of the snow capped summit looming just outside sturdy picture windows. Year round, there are likely to be folks snowboarding on the glaciers above you. If you want to experience lodging on the mountain as it was back in the first half of the twentieth century, spend the night. If you’re just stopping for a short visit, you could eat here or take something for the road as a picnic.

Continuing a few miles east on 26 you will have the opportunity to take an easy walk along an alpine lake at Trillium, Frog or Clear Lakes. You may be treated to picture postcard views of Mt. Hood reflected on the surface. Plus, some of these spots are home to letterboxes. If you want to have a picnic with a letterbox or two for dessert, continue east to the junction with route 216. Take 216 for five miles to a right turn for Bear Springs. A campground will be on the right and picnic areas on the left.

To return to 26 eastbound you can double back the way you came or continue two miles south on the good gravel road past the picnic area. You will soon be on reservation lands belonging to the Confederated Tribes of Warm Springs. As you travel further east, you can watch as the forest changes dramatically from deep green Douglas firs, to stately orange-barked Ponderosa pines and then sagebrush desert dotted here and there with juniper trees.

The High Desert

Two hours east of Portland you will descend into a deep canyon, entering the small tribal community of Warm Springs. If you’ve always wanted to sleep in a teepee and soak in hot mineral waters, now’s your chance.

Keep in mind that you can always rent camping gear at REI in Portland. In addition, the Museum at Warm Springs is a wonderful stop, a place to learn about the culture of the original inhabitants of this high desert terrain.

As you cross the Deschutes River, a premier fly fishing destination, you will be leaving Indian lands. Here cowboys and agriculture are the order of the day. Watch for hawks and eagles along the wide open stretches of road. The fields around you grow alfalfa hay, carrot seed, onions, mint as well as native grasses and other ornamentals. At the small town of Madras go south on highway 97.

Seventeen miles south of Madras you will cross the deep Crooked River Canyon. Do stop here at the Peter Skene Ogden Wayside for breathtaking views of sheer basalt walls droppping three hundred feet to the rocky river below. Your camera and logbook would both come in mighty handy here.
Nine more miles south will bring you to the small town of Terrebonne, gateway to Smith Rock State Park. You could easily spend an entire day in this park, hiking the trails and searching for letterboxes, surrounded by spectacular volcanic formations. Do remember to bring your own food and water as there is none available once you are inside the park. There is, however, yummy huckleberry ice cream sold at the rustic store just before you enter the park.

Continuing south from Terrebonne, you will enter the town of Redmond, home to two of Central Oregon’s most prolific letterboxers. As a result, there are loads of boxes to find in the immediate area. Move on to Bend and you will find the same variety of boxes by both locals and out-of-towners who have vacationed in this charming high desert town. A worthwhile stop between Bend and Redmond is the wonderfully wacky Petersen Rock Gardens, a folk art extravaganza.

Just west of Bend is Tumalo State Park. A couple of years back, a group of letterboxers monopolized the yurts here during spring break and seeded the park generously with boxes. If you have a yen to sleep in a yurt, you can rent camping gear at REI in Bend and have a go here. There is also another McMenamin brothers offering in Bend, the Old Saint Francis School. Stop for a meal or spend the night. You will not be disappointed.

A nice loop back to the Willamette Valley and Portland takes you west from Bend on highway 20 to the quaint Western town of Sisters. About twelve more miles west, you can take the turnoff to Camp Sherman, a flyfisher’s mecca. Grab a delicious sandwich at the Camp Sherman store and head for the headwaters of the idyllically beautiful Metolius River. Here you will see a crystalline river spring full-sized from the earth. A riverside hike here could result in lots of lovely new stamps in your logbook as well.

Continuing west on highway 20 over Santiam Pass, you will have great views of the stunning volcanic Cascade peaks. Fork Northwest on highway 22 towards Salem and in a couple of hours you will be at I-5 in the state capitol, Salem, where you can stop to see an amazing carousel handcrafted by contemporary artists or head north back to Portland. Enjoy!