Ultimate Bucket List 2023 for Portland, Oregon

Portland, Oregon:

Funky Fact: Portland, Oregon is the most bike-friendly city in the U.S.A.

1. Raven’s Manor

Downtown Bar with a dark creepy haunted manor theme. Specialty seasonal drinks range from $12-18. This place can be packed and bar seating is limited. They stop bar seating an hour before close. You can also book a specialty experience that includes a horror escape room for $55 per person.

Webpage and Information: Raven’s Manor

2. The Aimsir Distilling Co.

Some of the best locally distilled drinks in town. The stunning bar reminds me of a speakeasy inspired by the Wizard of Oz in the Emerald City. Try the $10 tasting flight and the Sweet Manhattan. Hours are limited.

Webpage and Information: Aimsir Distilling Co.

3. Portland City Grill (Upscale City Views)

A bar with the best view of the city. Call ahead to make a reservation if you want a view or window seat in the restaurant. Try to arrive around happy hour for the best drink prices and sitting at the bar is easy if you don’t have reservations and just want a drink.

4. Departure (Swanky Rooftop Bar)

Stunning rooftop skylounge. The theme is modeled after a swanky futuristic Airport. Take the elevator up from The Nines Hotel. Ask to sit at the outdoor bar. Cocktails range from $15-20. Beers are $7-9. Anticipate a wait for a seat and try going on a Sunday night. There are two wings, the restaurant portion serves top dollar sushi. (They are currently closed for Kitchen Renovations)

5. Ground Control (Arcade Bar)

Youthful and hip arcade bar serving food, drinks and home to tons of arcade games.

6. My Fathers Place

Classic throwback bar with vintage 70s vibes, swag lamps and a dim lit ambiance.

7. The Bible Club

Crowded bar filled with prohibition theme decor. Victorian sofas and antique artwork fill the walls. Plan on over an hour wait to enjoy the vibes. Even bar seating is limited.

Webpage and Information: The Bible Club

8. Horse Brass Pub

Quirky old english pub full of history, charm, and wood carved rafters lovingly plastered with humor and antiques. Affordable and simple drinks.

9. McMenamins

Beloved funky chain of pubs. This franchise renovates historic properties and incorporates bohemian art filled flair with secret rooms, passport adventure books, and specialty holiday events. Check out a Movie at one of their theater locations and try the cajun tots. Kennedy School, Edgefield, Crystal Ballroom, and the Backstage Bar at the Bagdad Pub are a few of the best nearby locations.

Webpage and Information: McMenamins

10. Moloko (Aquarium Bar)

Neon fish tank filled bar full of color and funk and unusual Art.

11. Psychic Bar

An eerie drink at the psychic bar is just what you need to find your center while strolling Mississippi Ave.

12. Bye and Bye

Fabulous drink menu with southern comfort flair. Try to arrive during happy hour 4-7 pm and try their vegan grub.

13. Radio Room

Fun and funky vintage Americana themed dinner. Come on the weekend for their Bloody Mary Bar and make sure to take a look at their heated rooftop patio (great at sunset).

14. A Roadside Attraction

*Cash only Bar* One of the most unusual bars in Portland, this place flies under the tourist radar. Its FULL of Asian and Maritime inspired antiques, vintage trinkets and oddities. If smoking bother you, this may not be your bar. Bring cash and enjoy the odd seating options. There is also an ATM inside.

15. The Coffin Club

*Cover Charge* Often entry requires a cover for the live band. This dark goth bar has dead horror-themed decor, and is a dance club that hosts rotating bands in a fog filled haze of lasers and black lights. Mixed Drinks $7-11. Great Vegan bites for $10.

16. Creepy’s

Somewhere between a vintage toy store, a bar and a gallery of velvet clown paintings. This bar has a unique theme and warm cheery vibe. Mixed drinks $10-11.

17. Pips and Bounce

Yep, that’s right. This is a ping pong bar! 10 pong tables are priced at $16 for 30 min. of table time. Check their Happy Hour deal: free 30 min. of table time
when you buy 2 alcoholic beverages. Mixed drinks $8-13. Cheap tallboys as well.

18. The White Owl Social Club

Fun and youthful tequila bar with a floral modern feel. Try them on Tuesday, when you can score $2 tacos.

19. The Blue Diamond

Home to live jazz and oldies, sung by some of the most talented voices in Portland. The crowd is usually made up of those 50+. Cheap drink, small dance floor and amazing shoestring french fries.

20. Wyrd Leatherworks and Meadery

A viking bar for mead lovers in a downstairs hideout complete with mediaeval armor, fur pelts, roaring fires and a leather craft gift shop. Stay for last call and enjoy the beat of drums and blow of carved horns.

21. Saraveza

Craft brewery filled with 1940s vintage coolers full of take home beer. Kind staff and good food and in full supply. Bottleshop beers $6-12

22. Victoria Bar

Enjoy the victorian vibes at the wrap around bar. This drinking parlor also serves vegan eats. Go for the Happy Hour Monday to Friday 3 – 6pm. Mixed drinks $12-14.

23. Holy Ghost

A mezcal and classy margarita lovers delight! Try the watermelon margarita with a pop-rocks rim. Mixed drinks $10-20.

1. The Morrison Street Mini Gallery

A very tiny street side, art gallery the side of a mailbox. Home to magical art that changes seasonally. Free and open 24h.

2. Ramona Quimby Statue

A charming bronze statue and fountain for the beloved Beverly Cleary’s characters Ramona, Henry and Ribsy the dog. These statues sit in Grant Park, near the Beverly Cleary School. The fictional literary character Ramona lived and adventured in Portland.

3. Portland Sign

One of two famed signs that represent Portland. This vertical beauty is in front of the Arlene Schnitzer Concert Hall.

4. Weather Machine

A useless but fun functional art piece located in Pioneer Courthouse Square. The Weather Machine displays a prediction of the weather every day at 12:00pm.

5. Freakybuttrue Peculiarium-Museum

*Not recommended for children* This odd museum is home to strange exhibits, sci-fi memorabilia, horror theme sets, cryptids, and mysterious oddities. They also sell artwork and merchandise in their gift shop. Free for persons wearing awesome costumes, otherwise plan on a $7 admission.

6. Glowing Greens (Pirate Glow MiniGolf)

A wonderful 13 hole blacklight mini-golf adventure. Price varies and is roughly $28 for 2 people. Book a timeslot slot online.

7. Horse Rings

Pay attention because scattered throughout the city are fun remnants of Portland history. These rings date back to the late 1800s. When riding a horse was key to getting around the old logging town. These horse rings are iron or brass loops fixed to curbs where a horse would be tied off on a main street. Portlanders wanted to preserve this piece of history and when sidewalks are repair they can be replaces by nearby homeowners for a small fee.

8. Portland Stag Sign

9. Salmon Sculpture

Beautiful outdoor sculpture piece titled “Transcendence” on Southwest Salmon Street and Southwest Park Avenue in downtown Portland.

10. Bart Simpson

11. SPIN Laundry Lounge

Fun and functional SPIN is a bar, eatery and laundromat all in one. They also house arcade games to entertain you while you wait for your laundry.

12. Peacock Lane-Seasonal x-mas Street

A seasonal favorite. This street is packed with tourist and locals who love the Christmas season. Almost every house on the block is decked out in colorful lights with some homes choosing themes. Go during the week in mid-December for a smaller crowd.

13. Movie Madness Video Rental and Memorabilia Museum

Part museum for movie memorabilia and park movie rental store. This Portland gem has been around for over 30 years and has thousands of titles. They specialize in hard to find films and cult fiction. They also have movie showings.

14. The Wishing Tree

A oddity unique to Portland this stunning old growth horse chestnut tree is covered in wishes. Its located on Northeast Morris Street and 7th Avenue and has been granting wishes since 2013.

15. Paul Bunyan Statue

A tribute to the mythical man Paul Bunyan. It’s said he lived in the Pacific Northwest or Canadian woods and made his living during the early 1900s during peak of the logging industry. This statue was erected in 1959 to commemorate the centennial of Oregon’s statehood. You can find him towering over the intersection in the Kenton neighborhood.

16. Pioneer Courthouse Square Signpost

Quirky direction marker which tells direction and distance to nine sister-cities and many useless geographical destinations.

17. Zelda Dog Fountain

This cute sculpture fountain is modeled after a real pet English bulldog names ‘Zelda Wisdom.’ In 2010 this sculpture opened in front of Portland’s Heathman Hotel. The pooch is dresses as a Heathman “beefeater” doorman.

18. Umbrella Man

Umbrella Man” also called ‘Allow Me’ is a 1983 full scale bronze sculpture, located in Pioneer Courthouse Square. Some call him the most photographed man in Portland.

19. Bubbler Fountains

Check out another historical landmark from 1912. Take a sip from one of the four-bowl Benson Bubbler fountains. Donated by Portland Philanthropist Simon Benson. In an effort to keep loggers out of the saloons at lunchtime and to encourage drinking water over booze. There are 52 of them today. Block a hole, or two, or three with your finger and watch the others shoot up wildly.

20. The Gold Door

Fanciful, odd, magical, macabre, cultural and mystical wonders await you at the gold door. Make sure to wander downstairs too.

21. House of Vintage, Red Light Clothing Exchange, Buffalo Exchange

Hawthorn is the local haunt for discount, vintage, used and recycled fashion. Check out House of Vintage, Red Light Clothing Exchange, or Buffalo Exchange to find just the perfect thing to add to your wardrobe. Each store offers different styles, make sure to bring your own bag!

22. Saturday Market

Since 1974 the Portland Saturday Market has entertained the city along Waterfront Park and Ankeny Plaza in Portland’s historic Old Town. It’s one of the most popular activities in the summer.

23. Paxton Gate

An unusual collection of taxidermy, skulls, bones, butterflies, preserved bugs, fossils, and crystals. They also have wall art, and a beautiful plant section. Perfect for finding treasures for your curio cabinet.

24. Powells City of Books

The best bookstore in the world. Ok, that’s my opinion. Powells has locations all over the city and deal in new, used and recycled books, art, stationary, games and art supplies. The sections twist and turn with funny, dark, quirky, and odd books. shelves are covered in book reviews, quotes and cool stuff all over the store. This is the best place to find travel souvenirs.

25. Mill Ends Park

The worlds smallest park. Sometimes its decorated, sometime its not. You can find it in the median strip of SW Naito Parkway and SW Taylor Street. It holds the Guinness world record for world’s smallest park with a total area of 452 square inches.

1 Doe Donuts

Better than Voodoo, I promise and almost no line. They are all vegan. Try the tiramisu it’s filled, has a coffee glaze and covered in cocoa powder. They have unusual flavors and seasonal unique pairings. At the end of the day selection is small, so go early. $3-4 each.

2. Mis Tacones

Vegan tacos with a colorful flair. Trans friendly and full of Art, color and fun.

3. Marrakesh

Amazing 5 course meal inside a cozy bohemian oasis. The interior is lavishly decorated and adorned with beautiful Moroccan tapestries, tassels and silver carved ornamentation. $25-30 per person for a 5 course meal. You may also see belly dancers jingling about the place. They are humorous, sweet and a cute extension of the ambiance.

4. Salt and Straw

Unusual ice cream flavor galore! Try the pear and cheese. Flavors rotate seasonally.

5. Papa Haydn

Upscale French restaurant know for opulent deserts.

6. Secret Pizza Society

Of all the flavors the Chalupa Batman is by far the best. The secret is in their amazing crust which is made from soft yet crispy focaccia bread. Did I mention, the pizzas are vegan?!

7. Food Cart Culture

Estimates say there are over 500 food carts around the city. Most lumped together as 2-3 cart mini pods. Some pods have a dozen or more. You can find some of the best food in town in these little cart pods. Some notable pods that offer great variety are Portland Mercado, Cartlandia, Piedmont Station Food Carts, Hinterland Bar & Food Carts and 5th Avenue Food Cart Pod. The larger pods usually have covered outdoor seating, a beer cart and some have live music and heaters for winter.

8. Bollywood Theater

Fantastic Indian street-food inside a funky bar. They also play old Bollywood films showing on a projector that drops down over a wall.

1 Mount St. Helens

On a clear day its likely you’ll catch a glimpse of the flat topped Mt. St. Helens to the north of Portland. From Portland its about an hour and a half drive. In the summer adventurers can climb up its ashy slopes to summit it. Check out the Ape Caves are the Guller Ice Caves if your looking for more interesting sites in the area. *Check if a forest pass is required for parking during your visit.*

2. Powel Butte

A stunning sunset or sunrise view of the city. This is one of the best places to watch for shooting stars on a clear night.

3. Mt. Tabor

Try and catch a stunning sunset as it reflects over the reservoir atop Mt. Tabor. If you are visiting during the summer check the time and date of the famed Soapbox Derby held here.

4. Laurelhurst Park

A 26 acre park with a huge duck pond and adorable boomerang island. One of the best times to visit is in the fall when the park turns a stunning yellow and orange.

5. Vista House at Crown Point Lookout

A secret spot many only visit during the day. Little do the tourist know, it comes to life on clear nights. This is the best place near the city to catch a small glimps of the Northern Lights during the right time of year. Not visible to the naked eyes. Photographers swarm here when weather patterns change and the Northern Lights swings down from Canada.

6. Clackamas River

Famed for kayaking, rafting, and floating. This stunning river offers stunning scenery in the spring, fall and summer. Many beaches along this river are also known for agates its a rockhounders delight.

7. Mt. Hood and Timberline Lodge

At 11,240 feet Mt. Hood is the tallest mountain in Oregon. A fun fact is that it’s the second most climbed mountain in the world (second to Mt. Fujiyama). One of the most magical places in Oregon is Timberline Lodge. Built in 1937, Timberline Lodge was crafted by artisans and filled with old growth wood, stone fire places, animal and nature carvings. This beautiful 55,000 square foot lodge is a must see when visiting. Try a cup of hot chocolate in the upper restaurant for a sugary treat.

Webpage and Information: Timberline Lodge

8. Japanese Garden in Gresham

The city of Gresham (just next to Portland) hosts a stunning (and free) Japanese Garden. Visit the cherry blossoms in the spring and the bright red and oranges in the fall for some brilliant color.

9. Rose Garden

The incredible International Rose Test Garden is nestled in Washington Park. its home to 10,000+ rose bushes with roughly 650 unique types. Bloom and be savored for May to early October. There is Paid parking but the Garden is free to all visitors. June is a magical time to visit and musicians and harpists frequent the garden.

10. Pittock Mansion

The Pittock Mansion is a French Renaissance-style château in the West Hills of Portland, Oregon, United States. The mansion was originally built in 1914 as a private home for London-born Oregonian publisher Henry Pittock and his wife, Georgiana Burton Pittock. The Mansion’s 23 rooms include a Library, Music Room, Turkish Smoking Room, Sewing Room, five large bedrooms, and two sleeping porches

11. Japanese Garden

Magic, peaces, and tranquility are the theme of this 1963 garden. Take an hour long stroll through the waterfalls, zen gardens, teahouses, streams and bridges. The garden also offers a stunning Mt. Hood view. Many visit for writing, drawing, photography or meditation. Admission is $12- 14.

12. South Blocks Park

This park is a 12-block greenspace stretching through the heart of downtown Portland. This park is home to 337 old growth elm, oak, and maple trees. A visit during the fall is a treat filled with crunchy leaves, and a cascade of yellow foliage that blocks out the sun and blankets the street in gold.

13. Tom McCall Waterfront Park

A stunning 36-acre park located in downtown along the Willamette River. This park offers spring cherry blossoms, summer fountains, rollerblading, biking, festivals and a Saturday market.

14. St. Johns Bridge and Cathedral Park

Known as the city of bridges this one holds a place in many Portlanders hearts. This Gothic-style cable suspension bridge spans the Willamette River and was built in 1931. Its easily the most iconic bridge in town and hosts the ‘Bridge to Brews race,’ an 8k & 10k walk/run in April.

1 Rimsky-Korsakoffee House

*Cash Only* A staple for lovers of the unique and quirky this victorian music theme coffee and desert restaurant targets the night owls, open 7 pm-midnight Wed.-Sunday. Report of this location being haunted are frequent. The upstairs bathroom is famed for its wildly odd under-the-lake theme including a ceiling mural and a full size kayak.

2. Tov Coffee and Tea

Its two magical themes in one. A Turkish tea shop inside a renovated double decker bus. Order downstairs and the friendly staff will sit you on the top level where the candles and ambiance will have you enjoying conversations for hours.

3. Petite Provence Patisserie

Everything on the menu in this French bistro will appetizers you. The glass case is filled with fresh baked bread, croissants, pastries, cookies and macaroons. I have glanced at their food menu, but I only every get one of the amazing looking deserts with a coffee of course.