1. St. John’s
The St. John’s neighborhood in North Portland used to be its own city before it merged into Portland. Come to St. John’s to see Cathedral Park which is just under the iconic St. John’s Bridge, whose large arches create a cathedral like setting right next to the Willamette River.
2. Mississippi Avenue
Mississippi Avenue in NE Portland, is what most believe all of Portland is like, odd and full of hipsters. Hipstery or not, no one can dispute that Mississippi is home to some of the best and most interesting bars, restaurants and stores in Portland. Have lunch at Por Que No? then bring your dog to grab a pint at Amnesia Brewing before catching a indie band at Mississippi Studious then take on “Das Boot” at Prost!
3. See a Timbers Game
There’s a reason why Portland is called Soccer City USA. People in Portland support their teams fanatically, but there is nothing like a seeing a Timbers game and their rabid supporters the Timbers Army. They will chant, dance and sing for their Timbers for all 90+ minutes. RCTID!
4. The Pearl District
Formerly the home to warehouses and light industry the Pearl has become home to a variety of art galleries, upscale businesses, bars and restaurants. If high class shopping is your thing you’ll want to spend a afternoon in the Pearl.
5. Get Lost in Powell’s Books
The largest independently owned and operated used and new bookstore in the world, Powell’s is a bookworms dream. Even if you aren’t a literary obsessive Powell’s is a great, quintessentially Portland, experience.
6. Look for the Portland inspirations behind the Simpsons
Matt Groening, the creator of the Simpsons is a Portland native and his hometown has been the inspiration for many things in the Simpsons. There’s Loverjoy St. and Flanders as well as many other streets in Portland who gave many iconic characters their names. Its pretty well known in Portland that the Simpson family are native Oregonians.
7. Pioneer Square
Officially Pioneer Courthouse Square, “Portland’s Living Room” serves as the heart of the city and is the site of dozens of planned and impromptu events, rallies and protests. While you are there see the “Weather Machine” where at noon each day the 33 foot column with a orb placed on top will announce the next days weather with a flash of lights and mist. Also see the sign post with the distance and direction to dozens of cities listed and the “Umbrella Man” a homage to Portland’s wet reputation.
8. The Bridges of Portland
With 10 bridges crisscrossing the Willamette its no wonder people also call Portland, Bridgetown. Beyond just being a critical means of getting around the city, the bridges of Portland play a important part of Portland’s culture. Every August cyclists gather for “Bike the Bridges” which involves crossing all of the bridges in a single day. In 2015 Portland will welcome the new Caruther’s Bridge which will serve as a crossing for bicycles, footraffic and the MAX.
9. NW 21st and 23rd
If you want to shop in Portland this is your neighborhood. Filled with hundreds of boutique stores NW 21st and 23rd is a mecca for shoppers who want a more local feel. The 21st, and 23rd are also the homes of dozens of incredible restaurants and coffee shops. Start a day off in NW at either Besaws with a Bloody Mary or a huge pancake at the Stepping Stone Cafe….that’s if you can stomach the wait.
10. See a Movie and have a Pint
Portland is home to dozens of renovated movie theaters where you can enjoy a beer while enjoying a movie. Many of these theaters, like the Bagdad, are run by McMenamins, a local brewer/restaurant company that renovates old buildings and transforms them into restaurants, bars or venues. Speaking of which…
11. Go drinking at the Kennedy School
The Kennedy School, is a old elementary school that has been renovated by McMenamins and turned into a playground for adults. Many of the old facilities have been turned into various small themed bars hidden throughout the school. You can enjoy a fine whiskey and cigar in what formerly was the detention room or put down some pints in the multi-level boiler room bar. If you need some time to sleep it off, just rent one of the former classrooms for the night.
12. Buy a CD at Music Millenium
In our digital music era, record stores are becoming quickly a thing of the past. Music Millenium continues to power on due to its loyal customers who still enjoy the record store experience. Long part of Portland’s musical scene, its a great place to check out before places like it fade away into memory.
13. Forest Park
One of the largest parks in US cities, Forest Park is incredible running, hiking and exploring opportunity right within the city limits. In a way a taste of the area before western pioneers arrived its a excellent place to experience the natural beauty of the Pacific NW right within Portland.
14. Portland Saturday Market
Every Sat and Sunday the largest continually operated outdoor market in the US sets up in the Old Town neighborhood. With 400 members, the Saturday Market has a near endless variety of vendors and artists selling their wears, and provides a opportunity to see of Portland’s more colorful residents.
OMSI (The Oregon Museum of Science and Industry) has been the necessary destination for kids and their parents for decades. Featuring exhibits on the local environment, the human body, engineering, as well as traveling exhibits, OMSI also features its own former military submarine the USS Blueback and the gigantic Omnimax screen which essentially is a domed IMAX. With its interactive exhibits, OMSI is fun no matter what your age.
16. See a Blazers Game
Until the Timbers moved up to the MLS in 2011, the Trial Blazers were Portland’s only professional team. While the Blazers have had their ups and downs, Portland’s Blazermania doesn’t seem to waiver. A new era seems to be starting with Damian Lillard being awarded Rookie of the Year. Ripcity baby! Ripcity!
17. The Oregon Brewers Festival
Home to more breweries (52!) than any city in the world, Portland aptly deserves its title as “Beervana”. The Oregon Brewers Festival is a 5 day celebration in late July of the Rose City’s favorite drink. In 2011 85 craft beers were represented and nearly 80,000 people attended over the course of the festival.
18. Have a Steak and show at the Acropolis.
In addition to having the most breweries as any city, per Oregon’s strong free speech protections, Portland hosts the most strip clubs per capita. With naked bike rides, burlesque shows and sex toy stores, Portlanders aren’t squeamish about sexuality. The Acropolis in SE Portland has actually come to some critical acclaim being named one of the best steakhouses in the US, but if steak isn’t your thing you can check out the vegan Casa Diablo in NW.
19. Hawthorne District
Portland’s version of Height-Ashbury (albeit not as extreme) is the center of the more counter-cultural aspects of Portland. Its been increasingly gentrified but still retains the more laid back atmosphere and “Keep Portland Weird” spirit.
20. First and Last Thrusday
First Thursday, is a monthly opening of the art galleries in Portland where people can walk from gallery to gallery enjoying the new exhibitions, fine wine and music. Last Thursday is a monthly art event where artists, musicians and performers gather together in the Alberta neighborhood in a much more block party atmosphere. Both are fun and unique ways to get to know the Portland art scene, if Last is decidedly stranger than First.
21. Have some wings at Fire on the Mountain
One of my personal favorite places to eat in Portland, Fire on the Mountain does have the greatest buffalo wings in Portland, if not the world. Get a dozen wings and fried pickle with a pint and enjoy. My favorite is their bourbon chipotle wings.
22. The Japanese Gardens
The Japanese garden in Washington Park, just up in the West Hills, is considered one of the best examples outside of Japan. The 5.5 acre garden is a serene and relaxing experience.
23. The Portland Farmers Market
Sitting at the top of the fertile Willamette Valley has been very good to Portland. With a variety farms not more than 20 miles outside the city and the ocean just two hours away, the Portland Farmer Market is well stocked with a variety of fresh locally produced produce, meat and seafood.
24. Food Carts!
There are nearly 500 food carts operating in Portland serving almost every kind of food imaginable. The highly competitive nature of the food carts ensures that the food will be some of the best in the city. Its very likely you could go months in Portland without having to cook in your home or step foot into a restaurant.
25. Getting out of Portland.
Portland is made great by not only what is in the city but what is outside of it. In a few hours you can go skiing on Hood, hike the Columbia Gorge, go wine tasting or spend a day at the beach then come back to Portland for the evening. Oregon’s immense natural beauty is part of what makes Portland such a great place to live or visit.
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