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Labor Day Weekend in Portland

Ask this member a question. Roadtravlr Die-hard weekender!
26 Sep 2006
3.5 of 5 stars based on 6 votes
This is an overview of my labor day weekend in Portland (2006), suitable for a solo travel or anyone with an appreciation of the quirky and locally authentic.

Time frame: Saturday to Tuesday
  • Explore locations featured in this Traveler List: Portland
  • Category: Perfect weekend
  • Traveler type: Culture, Sightseeing, Shopping, Never been before
  • Appeals to: Couples/romantics, Singles, Families with teenagers, Seniors, Students, Budget travellers , Tourists
  • Seasons: Summer
  • Tags: Labor Day, Art in the Pearl, quirky sites, thrift stores, cultural attractions
Day 1:
Start your visit with here, at a nice artist market and lots of yummy around--even happens on Sundays!
Walk around Pioneer Square, where all cross sections of Portlanders somehow come together. You might even find a group of DJs battling or a community fair happening. During my visit, the ACLU sponsored a "love rally" here.
3. Ground Kontrol
Take a short bus ride or leisurely walk to Ground Kontrol--A "retro" arcade for adults! Relive or play for the first time all the great games of the 70s and 80s, like Pong and Galaga! There is even a Doctor Who pinball machine. Great fun to be had here for just a quarter. At night this place comes alive as a bar and dance club.
Walk a few blocks here for great Thai Food--save room for dessert...the portions are quite generous!
5. Art in the Pearl
Day 2:

Start here at Portland's favorite annual arts festival!
an entire city block...filled with books! Heaven
After getting lost in all those books at Powell's, saunter over to the Buffalo Exchange on 1036 W. Burnside--just across the street. Lots of vintage and used clothes for great prices.
You've worked up an appetite finding cool threads to add to your wardrobe at the Buffalo Exchange. Walk a few blocks to Sushi Land for lunch--a place where you don't have to work for your food...it comes to you on a conveyor belt!
This is a super cool museum--velvet paintings galore! It's a small museum near the Hawthorne District...ran by Carl and Caren, a very nice couple. Admission is only $3.
Portland's version of NYC's Greenwhich Village or Seattle's Fremont--a really funky neighborhood with cool stores and unique people. Be sure to check out the Red Light District, a vintage clothing store and Greg's, a nice boutique with popular Asian trinkets.
I was lucky enough to catch Darcelle XV's "25th Annual La Femme Magnifique International Pageant" on the Sunday before Laby Day at the Oregon Cionvention Center. It is just like the Miss America Pagaent--but better and with world class female impersonators. Darcelle is another Portland institution and all the participants have true talent. Proceeds from the pagaent go toward local charities and community causes. Catch this show if it's around.
12. Oregon Museum of Science and Industry
Day 3: (Labor Day)

Called The Omsi by locals; great interactive exhibits and IMAX here. Be sure to take the submarine tour!
13. Tom McCall Waterfront Park
A great place to cap off Labor Day in Portland. Great views of the water!
14. Dante's Karaoke from Hell
Start the night right by being a legend in your own mind! On Mondays starting at 9pm, Dante's a great downtown bar, does live karaoke! The karaoke band is amazing and they will make you look good. The vibe is a nice and the food is just right.
15. The Grotto - National Sanctuary of Our Sorrowful Mother
Day 4:

A spiritual enchanted forest...five minutes from the airport. Not many locals even know about this spot--but this is a great way to start off a relaxing morning. Be sure to take the elevator ride to the upper gardens (only $3). Also a replica of Michaelangelo's Pieta is here.
16. Henry's 12th Street Tavern
A Portland institution. A great brewpub with an amazing selection of beers for all tastes. A few blocks down from Powell's.
So nice (and big) you gotta visit twice! Take another stroll through Powell's. Find that perfect book...or two...for the plane ride back home!
Art House movies with stadium seating--who could ask for anything more?!
After getting your read on at Powell's, walk a few blocks here for a thinking person's movie.
Explore locations featured in this Traveler List: Portland