The Long Weekend

The Perfect Weekend in Portland

Oregon’s largest city offers a unique set of attractions: Its metro area contains 37,000 acres of green space and, as the birthplace of culinary legend James Beard, unsurprisingly boasts an incredible foodie scene. Easily combined with a visit to Oregon’s Willamette Valley wine region, Portland offers outdoor adventures, a dynamic artisan community and ever-friendly locals. Here is a detailed itinerary for the perfect weekend in Portland.

Contact Indagare for assistance planning a weekend in Portland. Our specialists can book you at the hotel that is right for you and plan great meals and activities.

Day 1: Shop and Soak Downtown

With a population of just 600,000, Portland is deceptively large in area, encompassing many different neighborhoods, each boasting a distinctive charm. The downtown area, which has the most visitor attractions, is where the best hotels are located. We recommend the hip Ace Hotel for independent travelers, the Sentinel for traditionalists and the Nines, with its popular rooftop restaurant, for those seeking modern accommodations.

After fueling up, head to Powell’s City of Books, the largest independent bookstore in the world. Browse the rare titles here before moving on to the sprawling MadeHere PDX, which sells only made-in-Portland products (the Alma chocolate bars make great gifts). Next, head across the street to Union Way, a small shopping arcade that houses artisan candy company Quin and a Steven Alan boutique. Other downtown shops not to miss include Maak Lab, for natural cosmetics and bath products; North of West and WM Goods, for expertly curated fashion, home decor and accessories; Woonwinkel, for whimsical home furnishings; Frances May, for high-end fashion; and the Good Mod, for mid-century modern and custom furniture.

Build a little relaxation in on your first day with a visit to Knot Springs, a membership-based “social club centered around health, wellness and good times,” which offers visitors day passes to the spa, fitness facilities and hot springs circuit. After unwinding with aerial yoga or a massage, drive to one of Portland’s destination restaurants. Castagna is the city’s most high-end eatery, while Ava Gene’s serves delicious Italian dishes.

Related: Top Tables Portland

Day 2: Hiking and Food Cart Hopping

A paradise for outdoor enthusiasts, Portland’s metro area contains 37,000 acres of green space. The best attractions highlight the wilderness of the Pacific Northwest: Just beyond the city limits are such natural wonders as Mount Hood and the Columbia River Gorge. Begin the day with a hike through the gorge to the stunning Multnomah Falls, at 620 feet Oregon’s highest waterfall and one of its most scenic spots.

After freshening up at your hotel, indulge in a classic Portland experience: sampling cuisine from its many food carts. Food cart groupings, called “pods,” can be found on nearly every block, but the most famous is downtown, on Southwest 10th Street between Alder and Washington Streets. Here you will find the acclaimed Nong’s Khao Man Gai, which can be identified by the ever-present line of patrons eagerly awaiting the cart’s signature dish, Thai chicken and rice. Swing by the original Voodoo Doughnut, another place to expect long lines, for a sweet treat and the nearby Kiriko Made, which sells incredible products crafted from Japanese textiles, before hopping in the car to explore the Mississippi neighborhood.

One of Portland’s liveliest areas, Mississippi is home to one fantastic shops: Paxton Gate. The former is stuffed to the gills with such curiosities as carnivorous plants, taxidermied animals, framed insects and vintage scientific instruments, while the latter sells exquisite leather products made using classic tools and techniques, as well as other goods. After shopping, head to the rear of Tanner for a coffee and snack at the Wayback, the store’s cool bar and café.

Before twilight, drive up to the Portland Japanese Garden to experience one of the most authentic gardens of this kind outside Japan. With beautiful views of Mount Hood, this is a great place to watch the sun set.

Begin your evening with cocktails at Multnomah Whiskey Library, Portland’s most famous bar, with a speakeasy feel and more than 1,500 bottles of liquor on offer. For dinner, drive or Uber to Beast or Le Pigeon also among Portland’s best restaurants. The upscale prix fixe Beast is known for its nose-to-tail philosophy, often highlighting one animal a week and serving different cuts of it each day. Le Pigeon, owned by James Beard Foundation Award–winner Gabriel Rucker, serves such innovative dishes as beef cheek bourguignon with creamy cheddar and, for dessert, foie gras profiteroles.

Related: Top 10 Foodie-Friendly Cities

Day 3: Sights and Spirits

Get up early for a hike in Forest Park, more than 5,000 acres of woodland located just ten minutes by car from the downtown area. One of the most popular routes is a five-mile loop that passes Pittock Mansion and offers beautiful views of the Willamette River.

Grab a quick breakfast or lunch at Maurice, which serves light bistro fare inspired by Norway. Alcohol aficionados might want to take a Distillery Tour of the city’s southeast area, formerly a warehouse district, with stops at House Spirits, known for its Aviation Gin, and New Deal Distillery, which produces interesting vodkas infused with cacao nibs and Southwestern chili peppers. The more abstemious will find equally delicious teas on draft at Smith Teamaker. Before packing up to head home, stop at iconic Portland ice-cream shop Salt + Straw, which has locations throughout the city.

Contact Indagare for assistance planning a weekend in Portland. Our specialists can book you at the hotel that is right for you and plan great meals and activities.

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