Portland Travel Guide for First-Time Visitors: Where to Stay, Things to Do & Tips

The Neighborhoods of Portland; A Complete Guide

We ended up in Portland for a full month in September after our month-long stint in Seattle. Our only reference being Portlandia, we  were unsure of what to expect. We used trusted house-sitters once more, and found what turned out to be an amazing apartment right in the heart of the city. What immediately struck me was the hustle and bustle of the city. It was not as tall as Seattle or as  dense as San Francisco, but the foot and bike traffic there truly made it feel like a “happening” town. Less glamorized and publicized than other West Coast meccas, it truly was one of the most appealing places we nested in. The corner luxury apartment also helped.

Where to Stay, and Where to Visit, in Downtown Portland

One of the most appealing aspects of Portland is it’s walkability and connectivity. Not overwhelming in size or stature, it’s various neighborhoods are easily accessible from one to the next, and the major chunks of the city can each be covered in one afternoon. Though we had our free lodging provided, we did have some backup hotels mapped out in the Pearl District, in case our pet-sitting gig fell through.We had drinks and even checked out the rooms at several hotels in this area, each one a pleasant mix of updated accommodations and antique character. Though we did not need to, we recommend the Pearl District if hotels are your preference.

Being on the road, and on a budget, we were glad our accommodations had a full kitchen, and good access to grocery stores. We have always been quite adept at staying frugal by staying in to eat. It was, however, tough to stay in, as every restaurant was a refreshing departure from the repetitive chain restaurants that haunt most American towns. The establishments had fresh ingredients, with unique dishes and incredible flavors, making Portland one of our favorite food towns on the entire West Coast. The mom-and-pop smoke shops also saw low, low prices and high, high quality

Best Area to Explore in Portland; The Pearl District

In the northeast corner of town sits the old heart of the city, the trendy and terrace-lined Pearl District. Filled with foot-traffic and outdoor seating, the old brick buildings and wide, walkable streets made morning strolls and nighttime wandering a very pleasant experience. Centrally located to the rest of the city, even weekdays saw crowds of tourists and locals alike dining at the hot-spots long the main drag and meandering through the quaint craft shops and rugged outdoor stores scattered throughout the neighborhood. The nightlife here was busy but not overwhelming, offering an enticing social scene that was fun and lively but not obnoxious. A blend of many personalities, it is an excellent area of Portland.

The Best places to Eat in Portland

Not knowing what the cuisine of the Pacific Northwest entailed, we ended up finding some of our favorite spots in Portland. Life of Pi had the best pizza in town at an insanely good price. Down the street from our apartment was a tavern called McMenamin’s, an excellent go-to for happy hour snacks and drinks. Across the river, Katie O’Brien’s was our Sunday spot to watch all of our NFL games, if one has similar desires on a Sunday in Portland. The bar food there was phenomenal the numerous times we went, with the Club Sandwich and Corned Beef Hash being particularly memorable dishes.

Furthermore, not once were we bothered, or even asked a question, by any of these citizens of Portland. Ironically, that always makes you want to help that much more, and we did drop off some canned foods at one of the many mini-pantries found throughout the downtown area. It was obvious that residents cared for their fellow Portlandians, and it added to the immense communal feel that the city possessed. Many local run charities and organizations are dispersed throughout the town, offering services and much needed goods to the unhoused of Portland.

Why Portland is Worth the Visit

Despite any bad press, Portland is a refreshingly friendly city that offers endless good eats and pretty streets. The late summer air we found ourselves in was some of the best weather I have ever experienced, and the profundity of parks and scenic areas gave us daily reprieve from the “cabin fever” that road-trippers such as ourselves can be prone to. Nonetheless, we remember very fondly our month spent in Portland, and would definitely enjoy a trip back some day.

Best Neighborhood to Stay in Portland; Northwest/Nob Hill

The city as a whole was beautiful,  and we were glad we stayed on the west side of town along 23rd Street (top left of map). A very pleasant strip that was the perfect level of lively at night, it was lined with various independent restaurants, cafes and shops that are often hard to come by these days. The personality of the town was unquestionable in terms of presence, but debatable in terms of form. Eclectic residents representing all walks of live filtered in and out of the stores and eateries that litter all of downtown Portland. If AirBnbs are more your speed, this area of town will make you feel most like a local in no time at all.

Best Area to Bike around Portland; Chinatown and the Riverwalk Trails

On the East side of town along the Willamette River sits Chinatown, an area of Portland filled with beautiful brick buildings and an enjoyable maze of broad streets and old back alleys. The heart of the old downtown, the antique architecture and aesthetic appeal of the district sets this area apart from the rest of the city. River cruises, which we regret not partaking in, departed throughout the day along the rivewalk that runs parallel to Chinatown. Various options, from standard sightseeing to sunset booze cruises, offer an easy afternoon activity or unique nighttime experience. If long walks with your earbuds in is more your speed, the various bridges that connect the two sides of the city offer beautiful views and a respite from the hustle and bustle of the town.

Best Restaurants in Portland: Tasty Thai Food and Fresh Baked Breads

Of the many pleasant meals we had while living in Portland, the ones that stood out the most were the family-owned Thai restaurants. Having both been fans of this cuisine for some time, we were blown away by several spots that often boasted very cheap lunch deals. Our go-to was Tara Thai, where the insanely cheap lunch specials still consisted of generous portions and outstanding flavors. If bakeries and cafes are your thing, many single-family homes converted into cute, independently owned establishments give no shortage of personality or taste. It is refreshing to be in a place where small businesses and restaurants, from craft shops to lunch spots, abound. The best bread and cookies, our basic staples, were at Ken’s Artisan.

Is Portland Safe? Of Course! (And be Cautious)

No doubt you may have heard some sad news stories of the homeless problem in many West Coast cities, with Portland being a particularly dire situation. Though much is often exaggerated for the sake of sensationalizing viewers, there are nonetheless disheartening scenes in various parts of the city. There are pockets of camps near the outskirts of town and under some overpasses. Some busier areas of town still saw the occasional encampment, and unhoused persons can be seen in most parts of the city (just like any major metropolis). Having always lived in an area where homeless people were common, it did not phase me as much as it may other people.

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