How to Spend an Awesome 48 Hours in Portland

Hip, progressive, lively, unique and eco-friendly, Portland is one of the best cities to visit in the USA and makes an awesome break for a few days or a weakened. If you want to make the most of your time there, here’s how you should spend your time in Portland, Oregon…

Day One: Morning

Start your day with breakfasts at Jam on Hawthorne. Make your way to the Portland Saturday Market to browse art. Afterwards, find a classic or modern tale at Powell’s City of Books. Then, take a stroll through the Rose Test Garden for a view of the many species of roses in Portland. Finally, indulge in a lunch break at the Pine Street Market. 

Breakfast at Jam On Hawthorne

Jam On Hawthorne - Portland

Start your first morning in Portland at Buckman District’s Jam on Hawthorne. This exclusive breakfast restaurant is known as Portland’s best breakfast establishment. They were voted Portland’s Best Brunch in the years 2018, 2019, and 2020 via the Willamette Week Best of Portland Reader’s Poll. 

Not only do they serve breakfast, but they also display awe-inspiring art. Their tables are adorned with bright designs such as florals. 

Sample their coffee roasted via Marigold Coffee. Pair your strong coffee with their delicious dishes such as Ed’s Scramble, Cheesy Poofs, vegan french toast sticks, vegetarian Cheech and Chong Scramble, and so much more. There’s even a kids’ menu if you are bringing the kids along on your trip to Portland. 

Be sure to check on Facebook before you go to see their breakfast special of the week. One week, their breakfast special was Croque madame.

Once you are done eating your breakfast, be sure to pick up a jar of their housemade jam to take home with you after your trip to Portland. 

Address: 2239 SE Hawthorne Blvd, Portland, OR 97214

Portland Saturday Market

Portland Saturday Market - Portland

Take the 8-minute drive to the Portland Saturday Market after breakfast. It’s known as the biggest operating outside market in the United States that has continuously stayed open for many years through its March through September season. 

Located in the Tom McCall Waterfront Park, you will have access to many art pieces such as paintings, handcrafted jewelry, handcrafted wooden boxes, graphics, vegan bath and body products, hand-carved candles, and so much more. 

Vendors at the Portland Saturday Market

Grab a hand-crafted ceramic piece to display in your home from Queen of Cup. 

If you like aromatherapy, you can stop by Soul Escentials for essential oils to put in an essential oil warmer, to make your bath bombs, or to put in your shower or bath to achieve relaxation and calm. 

Address: 2 SW Naito Pkwy, Portland, OR 97204

Powell’s City of Books

Powell's Books - largest bookstore in the world

Make the 10-minute drive from the Portland Saturday Market to Powell’s City of Books to go on the next stage of your day one morning adventure. 

If you are feeling peckish from walking around the Portland Saturday Market, you can grab a treat from their on-site cafe before or after you start shopping. 

To get an idea of what’s in store before you visit in person, browse their website by genre to select what you love to read to find a title in which you may be interested. 

Since their website only offers shipping to your home and not curbside pick-up at the local store, you would have to ask the bookstore representative if the title you desire is in stock. 

You can even “wing it” and just visit the bookstore to browse the shelves until you find a title that sticks out at you. 

Address: 1005 W Burnside St, Portland, OR 97209

International Rose Test Garden

The International Rose Test Garden

Take another 7-minute drive to arrive at the International Rose Test Garden inside Washington Park. 

With over 10,000 rose bushes and 650 varieties of roses, you will be amazed at the many colors and shapes of roses that are even before your eyes. Each year, about 10 to 20 varieties are placed amongst the 650 of them with new roses that have been released throughout the local market. 

Roses are more than just red. You may be lucky and find crossbreeds of pink roses, white, purple, black, or even yellow or orange. 

The roses are at their peak from late May through October, so be sure that your trip is during the spring or summer months to be able to see them on a beautiful sunny day. 

Address: 400 SW Kingston Ave, Portland, OR 97205

Lunch at Pine Street Market 

Pine Street Market Portland

It’s a 12-minute drive from the International Rose Test Garden to Pine Street Market in the Old Town District.

We can imagine after browsing the Portland Saturday Market and the Rose Garden that you have worked up an appetite for lunch. 

There are a variety of food vendors to choose from such as the Pine Street Taproom and Pleasure Burger. 

This is Portland’s first food hall with nine of Portland’s top chefs all under one roof. The newest attraction is the Pine Street Taproom which features cocktails, Bloody Marys,  and even lagers, seltzers, and stouts on tap. 

Since you just visited the International Rose Test Garden, round out your experience with the Rose Garden cocktail that includes empress gin, creme de violet, and lemon juice. 

You will just have to visit to see the food available because it is not listed on Pine Street Taproom’s website. 

Address: 126 SW 2nd Ave, Portland, OR 97204

Day One: Afternoon

From Pine Street Market to the Pearl District, it is only about a 10-minute drive or so depending on where you start exploring. 

Explore Pearl District 

Pearl District Portland

You can explore these attractions in the Pearl District including:

  • The First Thursday Street Gallery.
  • Deschutes Brewery & Public House.
  • Jamison Square (with a splash pad-like fountain for the kids). 
  • Oblation Papers & Press.
  • Recycled Chic Boutique.
  • Icebreaker. 
  • Keen Footwear.

Jamison Square

Jamison Square Fountain - Portland

Speaking of Jamison Square, this is along your route when you are exploring the Pearl District. This was the first park added to this local neighborhood. 

The square itself is named after William Jamison who had a crucial input in creating the River District of Portland. 

Besides interactive splash pads and other founds, you can enjoy statue art such as the Tiki Totems or Rico Pasado the bear. 

Address: 810 NW 11th Ave, Portland, OR 97209


Dinner at Doug Fir Lounge

Doug Fir Lounge - Portland

Make your way to the Buckman District’s Jupiter Hotel Portland after a 10-minute drive from Jamison Square and go inside to experience Doug Fir Lounge. 

Not only will you enjoy a delicious dinner menu, but you will also love the live music playing while you eat. Open show nights start at 7 pm and go on into the late night until they close at night. 

Dinner begins at 6 pm, so be sure to plan your day accordingly when navigating the Pearl District and Jamison Square. 

If you are vegan, you can even enjoy delicious dishes including jackfruit tacos, a vegan stew called Harissa Explains It All, and you can make the Fir Burger vegan with a Beyond Meat patty. 

Other delicious dishes include Shells & Cheese, Rose Garden Salad, and Eastside Chicken strips. 

Address: 830 E Burnside St, Portland, OR 97214

Central Eastside Breweries

Barley Head Brewery

End your night by having a few drinks with a Central Eastside Breweries tour which is only 4 minutes away from Doug Fir Lounge if you start with the Cascade Brewing Barrel House (address below). 

Cascade Brewing Barrel House has Easy Rider Flight and other beers on tap. 

Rogue Eastside Pub & Pilot Brewery has many rotating taps with their main selections including Dead Guy Ale, Colossal Claude, Batsquatch, and more. 

Lucky Labrador Brew Pub on Hawthorne has many alcoholic beverages on tap including Black Sheep IPA, Blue Dog Pale Ale, Chocolate Stout, and more. 

Ground Breaking Brewing is a gastropub with gluten-free beer such as Inclusion dry-hopped pale ale, Dark Ale, and IPA No. 5. 

Address: 939 SE Belmont St, Portland, OR 97214

Day Two: Morning/Afternoon

Start your next day off by sleeping in a little extra at your hotel until it is time to check out. Try not to fill up on your hotel’s free breakfast (if they have that amenity) so that you can enjoy brunch at Off the Griddle. 

Brunch at Off the Griddle 

Off the Griddle Portland Oregon

Off the Griddle is a vegan and vegetarian restaurant with a delicious brunch menu. Try the Breakfast Burrito, Chorizo Burrito, Rise ‘N Grind Sandwich, Meatloaf Benedict, Berries and Cream Waffles, or the Mushroom Melt Waffle.

Address: 6526 SE Foster Rd, Portland, OR 97206

Portland Aerial Tram

Portland Aerial Tram Oregon

Take the 16-minute drive after your brunch to arrive at the Portland Aerial Tram. 

The Portland Aerial Tram is a gondola lift station located in South Portland’s Waterfront District. It’s one of the only aerial trams throughout the United States. Get great views of the Waterfront District into Marquam Hill when you ride the Portland Aerial Tram. Go from S. Moody & Gibbs in the Waterfront District to the Kohler Pavilion on the Hill.

Address: 3303 S Bond Ave, Portland, OR 97239

Voodoo Donuts

Voodoo Doughnut Portland

Say that you end your tram ride at the Kohler Pavilion. Hail a taxi or a Lyft driver to get you to Voodoo Donuts in the Old Town District so you can grab a delicious snack. 

Try their Cherry Time donut, Pineapple Canolo, or their Chocolate Coconut Canolo. If you feel like toting around extra donuts, grab a Classic Dozen, Voodoo Dozen, or Vegan Voodoo Dozen of donuts for the road. 

Address: 22 SW 3rd Ave, Portland, OR 97204

Portland Art Museum 

Portland Art Museum

You can take an 18-minute walk or hail another public transportation option to get to the Portland Art Museum in Downtown Portland. 

This art museum was founded in 1892 and is one of the oldest art museums located on the West Coast. It’s also known as the 7th oldest museum in the United States.

Check their website for special art-viewing exhibitions. There are art paintings, sculptures, and other pieces featuring African art, American art, ancient art, Native American art, and so much more. 

Address: 1219 SW Park Ave, Portland, OR 97205

Picnic at Tom McCall Waterfront Park

Tom McCall Waterfront Park - Portland

Take the 13-minute walk to the Third Avenue food cart pod which is right nearby the Tom McCall Waterfront Park so that you can choose your lunch. 

Once you have chosen what you will eat whether a noodle bowl at Stretch that Noodle or a cheesesteak at Buns on the Run, you can sit by one of the picnic tables near Tom McCall Waterfront Park for a relaxing picnic. 

If you already packed your lunch at your hotel, you can skip this step and go straight to the picnic tables at the waterfront park. 

Address: 98 SW Naito Pkwy, Portland, OR 97204

Browse quirky shops and boutiques on Northeast Alberta Street

Boutique shopping in the Pearl District

Hail public transportation to take the 17-minute drive to Northeast Alberta Street so that you can browse the quirky shops and boutiques there. 

Choose from Frock Boutique, Amelia, Modo Boutique, Tumbleweed, Demimonde Studio and Shop, and more. 

Address: NE Alberta St, Portland, OR 97211


Dine at Tusk

Tusk Restaurant in Portland

Call Lyft to take you 11 minutes down the street to Tusk, which is a Middle Eastern restaurant located in the Buckman District. 

Try their Mezze Platter for delicious fruits and vegetables with hummus. You can also try falafel and labneh, roasted delicata squash, cauliflower and broccoli salad, miso roasted cabbage, and half roasted chicken. 

Address: 2448 E Burnside St, Portland, OR 97214

Cocktails at Teardrop Lounge

Teardrop Cocktail Lounge

End your final day in Portland by hailing a taxi to make the 10-minute drive to Teardrop Lounge with delicious cocktails. 

Playboy Magazine Names Teardrop Lounge as one of the Best Bars. Portland Monthly considers Teardrop Lounge a Bartender of the Year. The lounge has many other awards that you can check out on their page. 

Try their cocktails such as Hell or High Water, Event Horizon, Windowsill Spritz, and others. 

Address: 1015 NW Everett St, Portland, OR 97209


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