Portland, Oregon has long been regarded as a bastion of progressive America. Therefore, it is no surprised the city has developed into one of the most GLBT affirming locations in the country. Portland is also renowned for its well-developed food culture. Though the winter can bring an abundance of rain, Portland has a pleasant climate year-round. Any season is in-season for the City of Roses.

Books, books, books and books plus some more books can be found at Powell’s City of Books in the Pearl District. The City of Books is the largest independent new and used bookstore in the world. It takes up an entire city block and features about 1.6 acres of retail floor space. With millions of volumes to choose from, you never know what gems you might find browsing the aisles. The books are well organized, not helter-skelter like some used book stores, and new and used books are shelved together. I have never placed a book store on my ‘must-visit’ list before, but I would be doing you a disservice if I did not implore you to visit Powell’s.

Just a short walk from Powell’s is one Portland’s premier boutique hotels, The Hotel Monaco. The Monaco is a property of the uber-GLBT friendly Kimpton Group and lives up to that chain’s reputation of class, sass and style. The hotel is housed in a historic department store building and, unlike many conversions, the rooms are spacious. I recommend upgrading to one of their King Suites, with a pull-out sofa bed, for families or those of us who really like to spread out. The Monaco is very pet-friendly, it even has its own mascot that roams around the lobby at times. One unique feature of The Monaco is its nightly complementary wine reception. At the reception you can learn the art of wine tasting or pick up a paintbrush and used the provided canvass to create your own work of art.

The Hotel Monaco shares a building with one of Portland’s premier dining establishments, The Red Star Tavern and Roast House. Dinner here is not cheap, but you do get what you pay for. The ‘New American’ style menu includes ample choices for even the pickiest eaters and the restaurant is suitable for kids. The menu includes a Chef’s Tasting Dinner, and I always order that when available. Tasting Dinners are an excellent way to experience food you wouldn’t have otherwise ordered, and I have never been disappointed with something the chef has sent to my table. The seasonal tasting menu during my visit included Marinated Big Eye Tuna, a surprisingly delightful Celery Root Puree with Crispy Sweetbreads, perfectly Seared Sea Scallops and some impossibly tender Wood Grilled Kobe Beef. The dessert featured Toasted Coconut Ice Cream that was so amazing I must give a shout-out to Pastry Chef Amy Nack.

An important thing to remember while in town is that most dining establishments here, including the Red Star, have some sort of happy-hour featuring appetizers and drinks. Taking advantage of this is an excellent way to get some good eats cheap in the early evening. One of my favorite happy hours is at the eloquent Heathman Hotel.  Here a satisfying meal for three, with drinks, will run you about $20. Make sure your there for happy hour though, the prices do go up!

After nibbling on finger foods for a happy hour dinner you will want to head to Cacao to top things off with a cup of warm drinking chocolate. Cacao is an amazing chocolate boutique that will enthrall any lover of the confection. Grab a mug of the drinking chocolate and then browse the selection of gourmet and imported chocolate bars, mixes and candies. They also offer a selection of local and international chocolate pieces for sale by the piece. If you have even passing interest in Chocolate then put a visit to Cacao on your list.

Great books and food are fine but Portland also has a remarkable gay nightlife. There are clubs for just about every ‘interest group’ out there. CC Slaughters is a mega-dance club with plenty of gyrating boys and stationary boy watchers. CC’s is also cover-free on most weekends so it doesn’t cost you anything to just stop in and look around. Darcelle XV shares a block with CC Slaughters and is considered to be the oldest drag club on the West Coast. Lots of straights come to get a look at the show but plenty of queen-loving gay folk hang around too. Eagle PDX Underground is the place to go if you are looking for the leather or bear scene. I didn’t make it by there but Byron Beck of Willamette Week tells me it is also a hang out for skater boys. Finally, if you just looking to see some skin and throw away a few one dollar bills head to The Silverado. There are plenty of other good clubs in town so feel free to explore!

When you wake-up from a long night at the clubs, or the opera, I recommend visiting Isabel for some late morning Coconut French Toast. Isabel is one of the latest gems in Portland’s dining crown. This small, modern, informal eatery is not to be skipped.

The city of Portland is surrounded by some of the most beautiful landscape in North America. I was blessed with a wondrous view of Mt. Hood from my downtown Portland hotel. There are many options for day trips or extended stays in the areas surrounding the cities and I encourage you to do some research and take advantage of them if you have the time. Their mountains make our mountains look like hills.

Getting around Portland is a generally pleasant task; the mild weather and flat terrain encourage walking to nearby destinations. A downtown hotel, like the Monaco, will put you within walking distance of most of where you want to go. There are a few places that might be slightly out of reach so you will want to become familiar with MAX. MAX is Portland’s light rail system and has a ‘free ride zone’ covering most of the city center. 

Portland is a delightfully diverse city that welcomes all folk enthusiastically. Singles, couples and families with older children will have plenty of fun to make the trip worthwhile.  I have one small caution: The flights between Nashville and Portland are long, so wear comfortable clothes and bring something to keep everyone occupied. 

Enjoy your trip!

This article has been republished from Out & About Nashville, and was part of a series of first-person pieces written by the late Bobbi Williams.

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