Travel Guide: A Weekend in Portland

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Is it possible that I could still be full from my trip to Portland a few weeks ago? We ate ALL. THE. THINGS! You always hear people saying that Portland has an amazing food scene and now I can truly vouch for that (my tummy, too!). I’m not 100% sure why it is but in chatting with some of the locals it seems like a lot of amazing NY chefs move to Portland to open restaurants because the cost is much less. Whatever the reason is, I’m here for it. Welcome to the west coast, culinary masters!

Other then the food scene there’s so much nature to be had and WINE… oh boy, did we wine! It’s always nice to visit a new city with a local. Shout out to my friend Ashley (we met in Haiti), a Portland native, who created our amazing weekend itinerary.

Keep scrolling for a great long weekend itinerary plus over 75 recs from the EDPfam and spots I’ve hit on previous Portland trips.

P:S: you can see all our activities on my Portland Highlight on IG

Where to eat, play., and stay in Portland.

For this trip we stayed at the Woodlark Hotel in downtown which was perfectly central to ALL. THE. THINGS. Check out my hotel diary here.

Day 1:

Lunch at Pine Street Market: It’s a great food hall with a ton of different casual food options AND Salt + Straw’s only soft serve location: Wizbangbar. We opted for tacos which were delish and, of course, some soft serve; the first of many amazing ice cream treats during our trip.

Dinner at Palomar: yummy cuban restaurant. The guava daiquiri is strong and worth the brain freeze. Word is that they also have a rooftop bar but it was closed when we went.

Cuban Food in Portland at Palomar

View in Portland, Oregon

Salt + Straw Soft Serve in Portland, Oregon

Multnoma falls in Portland, Oregon

Day 2:

Drive to the Vista House: for a gorgeous view of the Columbia River. It’s a little touristy but so worth it to take in the scenery.

Pay a visit to Multnoma Falls: waterfall located on Multnomah Creek in the Columbia River Gorge. Nature at it’s finest if I might say! It’s a just a skip and a jump away from the Vista House so you can do them in one swoop then head back into the city for lunch.

Stop for lunch at Sugarpine Drive In : the menu is fresh and delicious American food like sammies, saladsa, and soft serve (of course). Rumor has it there’s an off-the-menu drumstick soft serve order! They also have froze which we 100% indulged in.

Don’t miss dinner at Tusk: a very highly recommended mediterranean restaurant that did not disappoint. Whatever you do get the baked cheese.

After dinner drinks at Hey love: great cocktails and great vibe. They call it a cocktail bar and house party all in one. The music genre changes nightly and there’s always a fun party on Sundays.

Sugarpine Drive In, Portland

Tusk Restaurant in Portland, Oregon

Where to Eat in Portland, Oregon

Cherries in Portland, Oregon

Day 3: Wine tasting day!

Probably best to rent a driver for this day. We did that super last minute but a quick google will give you plenty of options. One of the wineries also lets you bring in your own food, so we packed a big cooler full of cheese, charcuterie and all the accoutrements.

• Stop 1: Argyle - known for their bubbles. Great place to start and kick off the day. There’s some open area that is great if you have kids.

• Stop 2: Stoller - this place is STUNNING. It’s a full estate with a ton of open outdoor seating. Grab a picnic table, open up your cooler and enjoy. Honestly it made the most sense to just buy a bottle and enjoy with our food. The price was pretty reasonable, too! VERY family friendly. If I lived in Portland I would be here every weekend.

• Stop 3: White Rose Estate - the views are insane; it feels like Tuscany or the South of France. Much smaller tasting area and the price point is on the high end.

• Stop 4: Ponzi - another stunning property. We were a bit tired/tipsy at this point but I would definitely go back.

Soak up the wine with dinner at Tasty + Adler: centrally located in downtown with a savory menu filled with country style items. Andy and I went here last fall when we road-tripped through Portland. It’s indulgent!

Where to go wine tasting in Oregon - Ponzi Winery

White Rose Estate in Oregon

The best places to go wine tasting outside of Portland, Oregon

Where to go Wine Tasting in Portland

Day 4:

By day 4 you should be really full - hah! But it’s the last day to eat, so WHEN IN PORTLAND …

Brunch it at Hunnymilk: probably the best brunch I’ve ever had. It’s a pre-fixe for $23 with a sweet and savory option. They also start you off with churros and chocolate dip… so there’s that.

Walk around downtown and check-out the cute shops, Powells Bookstore, and have ice cream at Ruby Jewel.

Pre-dinner dranks at the Hoxton Hotel rooftop: great vibe, gorgeous view, and a lovely cocktails.

Eat one last time at Bamboo: delish Sushi spot in downtown. Garden of Eden roll, fried Cauliflower and Tuna Poke were excellent.

Close out that night at Abigail Hall: v chic cocktail bar in the Woodlark Hotel. Unique and sophisticated cocktails. Great for an after dinner cocktail or two.

Wall Mural Outside Portland, Oregon

Brunch at Hunnymilk in Portland Oregon

Bamboo Sushi in Portland, Oregon

Rooftop at the Hoxton in Portland, Oregon

TO EAT + DRINKS:

• Pine Street Market - food hall for great casual dining plus Salt + Straw’s Wizbangbar.

• Palomar - cuban restaurant with rooftop bar. The guava daiquiri is strong and worth the brain freeze

• Sugarpine Drive In - great for lunch. the menu is fresh and delicious American food like sammies, saladsa, and soft serve

• Tusk: mediterranean restaurant that does not disappoint. Whatever you do get the baked cheese. Don’t forget a reservation

• Hey love: great cocktails and great vibe

• Argyle Winery - known for their bubbles

• Stoller Estate - stunning, great for kids, and allows outside food

• White Rose Estate - higher price point wine with insane views of rolling hills and vineyards

• Tasty + Adler - centrally located in downtown with a savory menu filled with country style item

• Hunnymilk - probably the best brunch I’ve ever had. It’s a pre-fixe for $23 with a sweet and savory option

• Hoxton Hotel rooftop - great vibe, gorgeous view, and a lovely cocktails

• Bamboo - delish Sushi spot in downtown. Garden of Eden roll, fried Cauliflower and Tuna Poke were excellent

• Abigail Hall - v chic cocktail bar in the Woodlark Hotel. Unique and sophisticated cocktails. Great for an after dinner cocktail or two.

Recs from the EDPfam:

• Proud Mary USA - amazing brunch

• Stella Taco - lunch spot

• Kens Artisan

• Cheese and Crack - froze + torched brie

• Piazza Italia

• Andinas

• Whiskey Library - put your name in right when it opens

• 10 Barrel - get the pastrami fries

• Brewery Blocks

• Toro Bravo - best tapas

• Pepe Le Moko - cocktails

• Fifty Licks Ice Cream

• Rudy's Pizza

• Beirstein Bagels

• Tope

• Afuri

• Eem

• Enoteca Nostrana

• Ok Omens

• Departure

• Urban Farmer

• Pine st 8 Biscuits

• Beast

• Nongs

• Hat Yai

• Imperial - dinner

• Ava Gene's - make reservation

• Pa Dee - Thai

• Navarre- Underrated

• Casa Zoraya - Peruvian Food

• Pok Pok - Chicken Wings

• Lechon

• Besaws - Brunch

• Breakside Brewery

• Grassa

• Shalom Yall

• Hale Pepe

• Oven and Shaker

• Hairy Lobster

• Romtoms

• Church

• Doug Fir Lounge

• Revelry

• Punchbowl Social

• Tilt - good friend chicken

• Dixie Tavern

• Deschutes - amazing beer

• Ruby Jewel - Ice cream

• Le Bistro Montage

• The Barrel Room - dueling pianos, fun bar

• XLB - best dumplings

• Wailua Shaved Ice

• Por Que No

• Fried Egg Love - best breakfast sandwiches

• La Neta

• Olympia Provisions

• Huber's- spanish coffee

• Canard - brunch

• Kachka - infused vodka shots, potato pancakes and caviar

• Noble Rot - wine + views

• Cartopia

• Waffle Window

• Great Notion - good beer

• Quarter World

• A cena - local winery that’s fun for wine tasting

• Altabira

• Kiosko Cafe - great little coffee shop at the waterfront

• Pambiche - delicious Cuban

• Taqueria Nieve - good Mexican

Woodlark Hotel, Portland

Where to go wine tasting in Portland, Oregon

Having fun at the Woodlark Hotel, Portland

Picking Berries in Portland

TO PLAY + STAY:

• Woodlark Hotel - beautiful hotel in the heart of downtown. Very much OUR vibe with minimal decor and tons of greenery throughout the hotel. Checkout my full hotel diary here.

• Ace Hotel - if you’ve ever been to an Ace property their branding runs strong. Andy and I stayed here last fall and enjoyed how central the location was plus the coffee shop attached.

• Vista House - gorgeous view of the Columbia River

• Multnoma Falls - waterfall located on Multnomah Creek in the Columbia River Gorge.

Recs from the EDPfam:

• Portland Saturday Market

• Cathedral park

• Hike in the Columbia River Gorge + stop at Thunder Island Brewing Co.

• Portland Flea Market - last Sunday of every Month

• Shop - there’s not sales tax!!

• Hawthorne, Alberta, NW23rd - great spots for shipping

• Artifact: Creative Recycle - vintage shopping

Wine Tasting in Portland

Ace Hotel in Portland

Woodlark Hotel

Where to Wine Taste in Portland

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