The Nines is great. All the train lines run right by there. A car will be nothing but hassle in town. Rent one for the day if you want to go to Wine Country/ The Gorge/Mt. Hood. The outdoor deck at Departure (the bar) is amazing on a sunny fall PDX day.

Beer: You will literally be in Beer Central. Within a 20 minute walk are Baileys Taproom, Tugboat Brewing, Deschutes Public House, Rogue Brewpub, Bridgeport Brewing. A newish outpost of Bends 10 Barrel brewing is also nearby. PDX's local answer to the YardHouse is Henrys, located like most of these, in the Pearl District. For a little taste of Oregons awesome wine, try a flight at Oregon Wines on Broadway, Hip Chicks Do Wine or Enso Winery.

For interesting food, dine at the carts. Hit the downtown cart pods thurs and Friday. There is cuisine from practically every region in the world. (Georgian cart Kargi GoGo is a personal fave). On Saturday, the best open carts are under the Burnside bridge at Portland Saturday Market. For dinner, Nongs (mentioned upthread) is good, as is Andy Rickers Pok Pok in Southeast. Make reservations if you want to dine at the celebrated Le Pigeon or its downtown protégé Little Bird. Bluehour is quite nice for a high end evening, nearby Andina is Peruvian Tapas and famous for Pisco Sours. There are literally hundreds of really good places to eat!

Honestly, Many will disagree, but a long weekend is best spent in the city. Visit the Hoyt Arboretum (take a red or blue max train to Washington park) then walk down the hill to the Rose Garden for a taste of our amazing wilderness. Come back soon and visit the coast, the Gorge, The mountain, wine country, etc, etc

I hope you encounter some rain, as that is what PDX should experience in October. Unfortunately, we have had very little rain this year.