Portland is not like most major cities in the United States. The evidence? Powell's City of Books, a legendary independent bookstore that takes up an entire block. More breweries than any other city in the world (with 32, it’s lovingly nicknamed "Beervana"). Embraced by wilderness, like the massive tree canopies at lush Forest Park or the rare natural wetlands at Oaks Bottom Wildlife Refuge. All within Portland's compact city limits.

While "Keep Portland Weird" is an unofficial slogan, the sentiment behind it is the essence of this quirky, laid-back town. If you're planning a visit, you can help the effort by spending your time and money with local businesses. From bistros and bike shops to food carts and farmer's markets, there's no shortage of ultra-hip stores for you to peruse at your leisure.

Portland City Limits

Portland's quaint neighborhoods are teeming with more than enough gardens, boutiques, parks and galleries to keep you busy for days. But don't forget to venture outside the city limits. Imagine an outing to spend the day skiing or tasting at rural Willamette Valley, voted one of America’s most beautiful wine regions. You can also stroll along miles of pristine beach or hike the Gorge — all just 90 minutes from the city, which means you can make it back in time for refreshments.

To quote Loretta Lynn, "Portland Oregon and sloe gin fizz. If that ain’t love, tell me what is…” Portland has no shortage of fine eating and drinking establishments. Soak up your cocktails with some super decadent doughnuts at the 24-hour VooDoo Doughnut, or splurge on a meal you'll never forget at Le Pigeon if you're feeling game. Portland is also home to some of the best coffee in the U.S., so that should give you a little extra motivation to get an early start the next day.

Bring an umbrella if you're visiting between October and June. Like Seattle, Portland is known for a long rainy or drizzly season, typically lasting from late September to late June. If you like to stay dry, July and August are your best bet with typically only a 10% chance of rain.