Portland, Oregon

Oregon’s largest city, which has adopted the slogan “Keep Portland Weird” to promote local businesses, has one of America’s youngest populations. On my first visit I couldn’t help but gawk at the parade of sexy tattooed bartenders, waitresses, taxi drivers, bellmen and donut factory pastry chefs who seemed to own the streets. My attraction to the place and its people was abnormally severe. Whether sitting on my own sipping a cocktail at a speakeasy or hiking through a national park en route to a roaring waterfall, I was constantly reminded I was single and ready to mingle.

There is no better place in Portland to tap into the sexy hipster vibrations than at The Jupiter Hotel. The 80-room property, located in Southeast Portland on Burnside Street, is a renovated mid-century motor inn that has been reimagined as a funky boutique hotel. The lobby is “a little bit alfresco,” offering a tented canopy where sparkling chandeliers glow at night. In the morning, guests can be found sipping their morning coffee on pretty white furniture, surrounded by a fern and bamboo forest that offers a nice dash of calm-me-down Zen.

Rooms at The Jupiter are crisp meets minimalist, with complimentary coffee from local roaster Water Avenue, free WiFi, city bikes for rent, eco-friendly Natura bath products and friendly front-desk concierge service. Spotting a hotel-branded complimentary condom on my bedside table? The cherry on my sundae!

Have a gay ol’ time
If you’re looking to enjoy a sud-sloshed evening à la gay bar, there are two iconic spots you can’t miss. The local watering hole is Crush, and every third Saturday it’s the place to be as Burlescape entertains crowds with its “tantalizing temptation of burlesque and boylesque wrapped in a taste of tease.” If a bouncy nightclub experience is more your thing, head to Holocene. Since summer 2003, the 325-person venue has been throwing unforgettable dance parties and all manner of arts and multimedia extravaganzas that blur the line between highbrow and down-and-dirty.

Happy hiking in Mt Hood territory
Located along the Mt Hood Scenic Byway near the town of Welches, Wildwood Recreation Site is a day-use area that is home to the Cascade Streamwatch Trail and Wildwood Wetlands Trail. Visitors can explore natural stream and wetland ecosystems via accessible trails and boardwalks and observe native fish in a unique underwater viewing chamber. This 550-acre forested park includes outdoor kitchens, a scenic picnic site and ball fields.

Refresh yourself along Little Zigzag River by taking a walk upstream to the trail’s end at thunderous Little Zig Zag Falls. On a hot summer day, it’s a cool and pleasant hike. The auto route to the trailhead overlaps parts of the original Barlow Road, which Samuel K Barlow opened as a wagon route over the Cascades in 1846 to complete the Oregon Trail.

Sweet sips in Washington County
No visit to the Tualatin Valley is complete without a stop at SakéOne, the leading American-owned and -operated brewer of craft sake in America. Bottled under four distinct brands (Momokawa, Moonstone, G and Peaceful River), SakéOne leads the fast-growing category with distinct styles and a penchant for educating its visitors. I sipped through the entire range and was most smitten with the Moonstone flavour-infused collection, which includes Asian pear, plum, raspberry and coconut-lemongrass offerings. You’ll be inspired to shake up a few new cocktails when you get home!

Established in 1982, Montinore Estate is a family-owned vineyard and winery and is among the top 25 producers in Oregon (in terms of number of cases), as well as the largest certified biodynamic/organic producer in the state. Varietals grown include pinot noir, pinot gris, gewurztraminer, riesling and müller-thurgau. Be sure to sample a splash of the white pinot noir, an unusual vino with hints of quince paste, coconut and granny smith apple.

Dine around downtown
Chef Gabriel Rucker has been recognized as one of the top chefs in America, with menus that push the envelope on traditional dishes. Since opening Le Pigeon in June 2006, he has been named Portland Monthly’s Chef of the Year, The Oregonian’s Rising Star Chef, Restaurant Hospitality magazine’s Rising Star and one of Food and Wine magazine’s Best New Chefs; he was also a nominee for the 2008 James Beard Rising Star of the Year Award. Highlights from his petite dining room include glazed pigeon, fried gnocchi and build-your-own ice cream sandwiches featuring yeasted potato bun, salted honey ice cream and apricot jam.

A visit to Multnomah Whiskey Library is a wee-sippy-sloshed hour of escapism during which you’ll fall back in time to an authentic Prohibition-era ambiance. The interior of this speakeasy is staunchly masculine, with studly bartenders wearing formal vests and waxed whiskers and serving up classic Old Fashioneds and Manhattans with plates of elk tartare. Tableside cocktail service is a specialty of The Library, as are tastings, pairing dinners and other educational events. The collection is an awe-inspiring 1,600 bottles.

For the most up-to-date travel information on gay Portland, see our City Guide, Listings Guide, Events Guide and Activities Guide.

Read our guide to planning a road trip along the Oregon coast.

Also, find out why Portland is on our lists of 10 Great Summer Cities, 10 Great Wine Destinations in North America and 10 Great Destinations for Women.