From trendy Portland to the beautiful wineries of the Willamette Valley to the volcanoes of the Cascades, and the Columbia River Valley, Oregon is a great place to visit. Yes it rains, but the summers are glorious.

Itineraries

Eat & Drink

Avid Cider Co.

This Bend craft cidery offers up delicious, locally sourced ciders in its dog-friendly taproom. Try the blackberry cider; it’s one of our favorites!

Salt and Straw

This ice cream shop originated in Portland. It has since expanded to some other cities (like San Francisco), but the ice cream is wonderful. They have a rotating board of monthly flavors always using innovative and local ingredients, as well as regular list.

Willow

This is a small restaurant in Portland that offers a 6-course tasting menu for a reasonable price. They have 2 seatings a night, one at 6 and one at 8:30 in a restaurant that can fit 11 guests. It’s intimate, and the food is wonderful. Open Weds – Sat.

Multnomah Whiskey Library

This is a really cool spot which offers an exhaustive list of whiskeys as well as great food. The bartenders are true mixologists and whip up some wonderful cocktails. Make an online reservation for a seating.

Oui! wine bar and restaurant

Oregon is known for its wine and food. Why not experience both at the same time? You can get just a simple glass of wine, try a flight, grab dinner or do the best of all worlds with a flight and food combination.

Deschutes Brewery Bend Tasting Room

Deschutes is a fantastic craft brewery founded in Bend in 1988. Their brewery and tasting room offers one of the best brewery tours we’ve been on. The tasting room has a great selection or rare and hard-to-find Deschutes beers.

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Ned Ludd

This is a typical Portland eatery where dishes are cooked in a wood fired oven and served in a rustic room, farm-to-table style. Try the 3 course prix fixe with wine pairings on Sunday, Monday, or Tuesday.

Hopworks Urban Brewery

This is a great brewery across the river from downtown Portland. If you’re staying on that side it’s a very convenient stop, and even if you aren’t you may want to venture that way. The beer is Hopworks’ own, it’s great with tons of variety in flavor profiles and the food is really good as […]

Kachka

This is a distinctly Soviet flavored restaurant. The chef is a first generation American of Belarusian descent and the food consists of dumplings, skewers, smoked and cured fish, pickles, etc (along with a lengthy vodka menu). Ingredients are local and the food is great. It’s consistently one of the best restaurants in Portland.

Deschutes Brewery Public House

Deschutes started in Bend, Oregon and offers up fantastic beer. You can now find their beer at at restaurants and bars serving microbrews across the country, but you their Portland brewpub offers access to uncommon vintages that are tough to find elsewhere.

Pelican Brewery Company

This is a brewpub in downtown Cannon beach. They offer large flights and reasonably good food.

Pok Pok

This place started as a food truck and has now grown to three locations. It’s regularly on the Best of Portland lists for its mostly northern Thai food.

Portland Restaurant Scene

Oui! Wine Bar / Restaurant Willow Kachka Q Restaurant Expatriate Ripe Cooperative Le Pigeon Ok Omens Hat Yai Normandie Life of Pie Nuestra Cocina Bamboo Sushi Yama Sushi Departure Lounge Proud Mary Cafe (breakfast) Sweedeedee XLB Kim Jong Grillin Fried Egg (breakfast)

Voodoo Donuts

This has to be one of the most famous donut shops in the world. It’s still a hole-in-the wall operation and there are long lines. Are the donuts worth it? I mean, they’re donuts.

See

Crater Lake National Park

The second-deepest lake in North America lies in the crater of a dormant volcano. It boasts some of the most pristine water in the world. It’s also stunningly beautiful.

Oregon Shakespeare Festival

The Oregon Shakespeare Festival puts on some of the best theatrical productions in the world. People will vacation in Ashland to see the entire season catalog. Definitely worth a visit on your trip through Oregon.

Portland Japanese and Rose gardens

This place offers 11 beautiful acres of Japanese gardens. The famous and equally beautiful international rose garden is just across the street. You’ll see koi ponds, ornamental cherry trees, a ceremonial teahouse and a sand garden.

Powell’s City of Books

Powell’s is the largest independent bookstore in the world and a Portland Institution. It’s huge – they’ll give you a map it’s that big. Let your inner bibliophile go wild.

Ecola State park

This is a beautiful coastal park near Cannon Beach. Favorite walks are to Indian Beach and the Clatsop Loop Trail.

Lan Su Chinese Garden

This is a delightful little garden in downtown Portland. It’s a classic Chinese garden that houses ponds, pretty plants, and a traditional teahouse.

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International Rose Test Gardens

Portland is nicknamed the Rose City and after seeing these gardens you’ll be able to understand why. The gardens cover 4.5 acres and as you wonder you can enjoy fountains, a wide away of flowers (beyond the roses) and an incredible view of downtown Portland and, weather permitting, Mt. Hood.

Fort Clatsop National Historic Park

Lewis and Clark spent a very rainy winter here at the end of their journey through the American West in 1805-1806, and the cabins they built have been reproduced. It’s a pretty place to visit and in the summer there are living history demonstrations.

Do

Portland walking tour

For a great introduction to this beautiful city, try the Best of Portland walking tour.

Stay

Country Willows Inn

This gorgeous bed and breakfast just outside of town is our favorite place to stay in Ashland. The setting is beautiful, the food is delicious, and the owners are fantastic.

Timberline Lodge

A beautiful hotel on the slopes of Mt. Hood, Timberline Lodge is perfectly placed for skiing in winter and hiking in summer. The rooms are a little dated, and it can definitely be overpriced, but the views are unbeatable and the restaurant is good.

Arch Cape Inn and Retreat

This is a castle-like hotel in beautiful Cannon beach. It offers wonderful and comfortable rooms and a very good breakfast. It’s about 5 minutes south of town but a short walk to a lovely uncrowded beach.

Ace Hotel

This place is awesome. Both elegant and funky, it’s a great option in downtown Portland in easy walking distance of what you’ll want to do. The attached restaurant, Clyde Common, offers locally sourced food.

Hyatt House Portland downtown

This is a modern hotel near the river and downtown Portland. It’s right on a streetcar line to downtown making it a convenient place to stay. While we don’t tend to love big name hotels, the location and price make this a decent option.

The Society Hotel

This is a nice, more budget friendly option in Portland. Housed in a building which dates from the 1881, its a restored budget boutique hotel in downtown Portland with easy access to walking to all major sites.

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Lion and the Rose

If you want to stay in a refurbished Victorian house from the turn of the century with the charm of a B&B this place is probably right for you. The breakfast is phenomenal. The only downside about this B&B is that it’s further from downtown and you can’t walk.