Things

Portland stands out as a city that dances to its own beat, where the unofficial motto Keep Portland Weird isn’t just a saying – it’s a way of life.

Among the many things to do in Portland, visitors quickly discover that this Pacific Northwest gem offers experiences that go far beyond the usual tourist checklist.

The city pulses with creative energy, whether you’re exploring the warehouse-turned-art-galleries in the Pearl District or stumbling upon impromptu street performances in Pioneer Courthouse Square.

What sets Portland apart isn’t just its attractions, but its distinctive personality. Here, eco-friendly bikes share the road with vintage trolleys, coffee shops double as community gathering spaces, and neighborhood streets burst with colorful murals.

This guide will take you beyond the standard tourist spots to discover the authentic Portland experience – where locals find joy in the unexpected and visitors become temporary Portlanders themselves.

#1 Explore the Peculiarium

Step into the Freakybuttrue Peculiarium, one of the most unique things to do in Portland that perfectly captures the city’s love affair with the bizarre.

This off-beat museum stands as one of the true hidden gems in Portland, offering visitors a delightfully strange journey through oddities, art installations, and interactive exhibits that challenge your perception of reality.

Located in Northwest Portland, the Peculiarium houses an eclectic collection that includes:

• Life-sized alien autopsy scenes
• Bigfoot memorabilia
• Interactive zombie displays
• Unusual art installations
• Vintage sci-fi advertisements

What makes this attraction special isn’t just its weird exhibits – it’s the hands-on experience. Unlike traditional museums where touching is forbidden, the Peculiarium encourages visitors to interact with displays and even pose for photos in bizarre scenarios.

You can lie down on an alien examination table or peek into mysterious viewfinders showing otherworldly scenes.

The museum’s gift shop adds another layer of quirky charm, offering unusual souvenirs and locally made oddities that you won’t find anywhere else. They even serve unusual ice cream flavors with names that might make you question your dessert choices – but that’s part of the fun.

While not for the faint of heart (or those seeking traditional museum experiences), the Peculiarium represents Portland’s embrace of the unconventional. It’s a place where imagination runs wild and normal is nowhere to be found – exactly how Portland likes it.

#2 Visit the Witch’s Castle

Deep within Forest Park’s lush landscape sits one of the most intriguing must-see Portland landmarks – the mysterious Stone House, better known to locals as the Witch’s Castle.

This moss-covered stone structure, which ranks among the most fascinating free things to do in Portland, combines natural beauty with urban legends in a way that captures visitors’ imaginations.

Despite its spooky nickname, the structure was originally built in the 1930s as a park ranger’s station and public restroom. Time and neglect transformed it into the haunting ruins we see today, with nature slowly reclaiming the stone walls and creating an eerily beautiful scene.

Local folklore has woven fascinating tales around these ruins, ranging from stories of cursed land to tales of star-crossed lovers. While these stories may be more fiction than fact, they’ve helped make the castle a beloved spot for both locals and visitors alike.

The journey to the Witch’s Castle is part of its charm – a gentle 0.3-mile trail from Lower Macleay Park leads you through some of Portland’s most enchanting forest scenery.

Following the path along Balch Creek, hikers of all skill levels can enjoy the well-maintained trail year-round. The sound of rushing water and the crunch of leaves underfoot create a peaceful backdrop for this urban adventure.

The best time to visit is early morning when fog often shrouds the structure in mystery, creating an atmospheric experience that feels worlds away from downtown Portland.

Photography enthusiasts particularly love capturing the interplay of light and shadow on the moss-covered walls, while history buffs appreciate this unique glimpse into Portland’s past. 

Remember to bring a camera and wear sturdy shoes – the path can get muddy, especially during Portland’s rainy season.

#3 Experience the Portland Troll Bridge

Tucked beneath the Morrison Bridge lies one of the quirkiest fun things to do in Portland that perfectly captures the city’s creative spirit.

This peculiar spot, considered one of the lesser-known hidden gems in Portland, showcases a growing collection of plastic trolls that has transformed an ordinary bridge into a playful community art project.

The Troll Collection

What started as a few lonely trolls has grown into an impressive display:

• Hundreds of colorful troll dolls
• Vintage and modern varieties
• Some dressed in tiny handmade outfits
• Many arranged in whimsical scenes
• New additions appearing regularly

Finding the Bridge

Located near the east end of the Morrison Bridge, the troll collection is easily accessible from the Eastbank Esplanade. Look for the concrete support structure where fellow visitors often leave chalk arrows pointing the way to this unconventional attraction.

Community Connection

The tradition reflects Portland’s collaborative spirit, with locals and visitors alike contributing to the display. People often:

• Add their own troll dolls to the collection
• Rearrange existing displays
• Leave small treasures for the trolls
• Take photos to share on social media
• Create miniature scenes with the dolls

Best viewed during daylight hours, this quirky installation proves that Portland’s charm often lies in its smallest, most unexpected details. Remember to bring your own troll to add to the family – it’s a beloved local tradition that keeps this unique spot growing and changing.

#4 Discover Mill Ends Park

Among the many unusual things to do in Portland, visiting a park might not sound extraordinary – until you realize this one measures just two feet across.

Mill Ends Park, officially recognized by Guinness World Records as the world’s smallest park, ranks among the most delightfully odd best places to visit in Portland.

The story of this miniature marvel began in 1948 when Oregon Journal journalist Dick Fagan noticed a hole in the concrete median where a light pole was meant to stand.

Rather than let the space go to waste, he planted flowers and began writing about it in his newspaper column called Mill Ends.

Fagan crafted whimsical tales about a leprechaun colony living in the park, complete with a chief leprechaun named Patrick O’Toole, who supposedly granted him a wish in exchange for a home.

Over the years, this tiny space has hosted an impressive array of events that showcase Portland’s playful spirit. Locals have organized miniature celebrations, installed tiny art pieces, and even created microscopic swimming pools on particularly hot days.

During holidays, the park transforms with seasonal decorations, while St. Patrick’s Day brings special attention to its leprechaun lore.

Located at the intersection of SW Naito Parkway and Taylor Street, this 452-square-inch park contains a small tree (regularly changed), seasonal plantings, and a dedicated plaque explaining its unique history.

While the park’s size might limit your visit to just a few minutes, it perfectly represents everything Portland loves about itself – creativity, humor, and the ability to turn something ordinary into something wonderfully weird.

Just remember to watch for traffic when visiting this median-based marvel, as its location in the middle of a busy street adds another layer of quirkiness to this beloved Portland landmark.

#5 Enjoy Free Shakespeare in the Park

When summer arrives in Portland, the city’s parks transform into open-air theaters thanks to the Original Practice Shakespeare Festival.

This beloved tradition stands out among outdoor activities in Portland and ranks high on the list of family-friendly activities in Portland, offering a fresh take on classical theater that both entertains and educates.

Unlike traditional Shakespeare performances, these shows capture the spontaneous spirit of the Bard’s original productions. Actors perform with only a few hours of rehearsal, carrying scrolls with their lines and cues, just as performers did in Shakespeare’s time.

This unique approach creates an energetic, unpredictable atmosphere where anything can happen – and usually does.

The festival travels to different parks throughout the summer months, turning Portland’s green spaces into temporary Globe Theaters. 

Audiences spread blankets on the grass, unpack picnic baskets, and settle in for an evening of entertainment that feels both classical and distinctly Portland. Children especially enjoy the casual atmosphere, where they can move around freely and react naturally to the performance.

What makes these shows particularly special is their accessibility. There’s no admission fee, though donations are welcomed, and no need for formal attire or theater etiquette.

The actors interact with the crowd, explain unfamiliar language, and often pull audience members into the action, making Shakespeare’s complex works approachable for everyone.

Shows typically begin in early June and run through September, with performances scheduled during weekend afternoons and long summer evenings.

Bringing blankets, lawn chairs, and picnic supplies is encouraged, creating a festive community atmosphere that celebrates both culture and the outdoors.

#6 Float Down the Willamette River in a Hot Tub

In true Portland fashion, someone asked, What if we put a hot tub on a boat? and actually made it happen. Among the most outlandish fun things to do in Portland, floating down the Willamette River in a hot tub boat perfectly captures the city’s quirky innovation and love for waterfront recreation.

This unusual experience has quickly become one of the most talked-about unique things to do in Portland. Picture this: you’re soaking in steamy water while gliding past Portland’s skyline, the Hawthorne Bridge towering overhead as you toast with friends.

Each floating hot tub comes equipped with a certified captain who handles navigation, allowing passengers to focus on relaxation and sightseeing. The vessels maintain a comfortable 104-degree temperature year-round, making this activity enjoyable even during Portland’s cooler months.

The experience typically lasts two hours, during which you’ll cruise past some of Portland’s most iconic riverside landmarks. The boats accommodate up to six people, making it perfect for small gatherings, birthday celebrations, or simply an unforgettable afternoon with friends.

Music players, cup holders, and LED lighting create a party atmosphere, while the heated water keeps everyone cozy regardless of the weather.

Safety remains a priority, with life jackets provided and strict guidelines about alcohol consumption. Reservations are essential, especially during summer months when locals and tourists alike scramble to secure their floating hot tub adventure.

Early morning trips offer serene views of the city waking up, while sunset cruises provide spectacular views of Portland’s lights reflecting off the water.

#7 Visit Powell’s City of Books

Taking up an entire city block in downtown Portland, Powell’s City of Books stands as one of the most essential things to see in Portland and ranks at the top of any list of best places to visit in Portland.

This literary landmark isn’t just a bookstore – it’s a maze of knowledge spanning nine color-coded rooms across multiple floors, housing over a million books.

Entering Powell’s feels like stepping into a book lover’s dream. The blend of new and used books sharing shelf space creates a treasure-hunt atmosphere, where rare first editions might sit next to yesterday’s bestsellers.

The store’s famous map helps visitors navigate through rooms named after colors, each dedicated to different genres and subjects. The Pearl Room houses arts and literature, while the Rose Room celebrates the written word in all its technical glory.

What makes Powell’s truly special is its atmosphere. The creaky wooden floors, the scent of coffee wafting from the in-store café, and the quiet murmur of readers lost in their discoveries create an ambiance that keeps visitors browsing for hours.

Staff members, known for their encyclopedic knowledge, leave handwritten recommendations throughout the store, helping readers find their next literary adventure.

The rare book room on the top floor offers a glimpse into literary history, showcasing valuable first editions and signed copies behind glass. Meanwhile, the Northwest Reading Room celebrates local authors and regional history, connecting visitors to Portland’s rich literary culture.

Whether you’re seeking a specific title or simply wanting to get lost in the stacks, Powell’s offers an experience that reminds us why physical bookstores still matter in the digital age.

#8 Check Out the Zymoglyphic Museum

Tucked away in a South Portland basement lies one of the most fascinating hidden gems in Portland – the Zymoglyphic Museum. This tiny but captivating space ranks among the most thought-provoking unique things to do in Portland, showcasing an extraordinary blend of natural artifacts, artistic installations, and imaginative storytelling.

The term zymoglyphic refers to the art of creative fermentation, and this museum celebrates the beauty of decay, transformation, and natural processes.

Inside, visitors discover carefully curated displays featuring everything from rust-covered artifacts to intricate assemblages made from found objects. Each exhibit tells a story of metamorphosis, where discarded items and natural specimens combine to create something entirely new and mysterious.

The museum’s creator has developed an entire fictional world around these collections, complete with its own mythology, cultural artifacts, and natural history.

Visitors might encounter miniature landscapes populated by bizarre creatures, cabinets filled with curious specimens, and dioramas that blur the line between reality and imagination.

What makes this space truly special is its intimate scale and attention to detail. Unlike traditional museums, the Zymoglyphic Museum encourages close inspection and personal interpretation.

Open limited hours and by appointment, this small museum offers a deeply personal museum experience. The curator often provides guided tours, sharing stories about the collections and explaining the philosophy behind this unique artistic vision.

#9 Participate in PDX Sidewalk Joy

Take a stroll through any Portland neighborhood, and you might stumble upon miniature fairy gardens tucked into tree bases, painted rocks bearing messages of hope, or tiny doors leading to imaginary worlds.

PDX Sidewalk Joy, one of the most delightful fun things to do in Portland, transforms ordinary walks into adventures of discovery, making it one of the city’s favorite family-friendly activities in Portland.

This grassroots movement began when local artists started creating small-scale installations along neighborhood sidewalks, encouraging others to add their own creative touches to the urban landscape.

Today, these whimsical discoveries pop up everywhere – from decorated utility boxes to poetry chalked onto sidewalks, from painted garden gnomes to intricate yarn bombings wrapped around street poles.

The beauty of PDX Sidewalk Joy lies in its spontaneity and community spirit. Anyone can participate by either creating or discovering these artistic surprises. Local families often make scavenger hunt lists, checking off different types of installations they find while exploring various neighborhoods.

Neighborhoods like Sellwood, Alberta, and Hawthorne are particularly rich in sidewalk art, though these creative expressions can be found throughout the city.

The movement has even inspired several social media groups where participants share their findings and leave clues for others to discover new installations.

The initiative has grown beyond mere decoration, fostering community connections as neighbors share their creativity and inspire each other.

Whether you’re an artist contributing to the landscape or a explorer seeking out these hidden treasures, PDX Sidewalk Joy offers a uniquely Portland way to experience the city’s neighborhoods.

#10 Experience the Grotto

Carved into a 110-foot basalt cliff, The Grotto stands as one of the most serene must-see Portland landmarks, offering a peaceful retreat from urban life.

This 62-acre Catholic sanctuary has become one of the most enchanting romantic things to do in Portland, appealing to visitors of all faiths and backgrounds with its remarkable blend of natural beauty and spiritual artistry.

At the sanctuary’s heart lies its namesake cave, a stunning rock grotto housing a marble replica of Michelangelo’s Pietà. A network of winding paths leads visitors through meticulously maintained botanical gardens, where seasonal blooms create an ever-changing tapestry of colors.

An elevator whisks visitors to the upper level, revealing panoramic views of the Columbia River Valley and cascading mountains in the distance.

During December, the Grotto transforms into a wonderland of lights during the Festival of Lights celebration, when over half a million lights illuminate the gardens. Choral performances echo through the grounds, creating an ethereal atmosphere that draws visitors from across the region.

Throughout the year, the sanctuary hosts various cultural and spiritual events, though many visitors come simply to enjoy the meditative atmosphere and stunning landscaping.

The grounds feature several distinct areas for contemplation, including a labyrinth, multiple shrines, and reflection ponds. Native Pacific Northwest plants mingle with ornamental species, creating peaceful havens where visitors often spot local wildlife.

The combination of natural cliff walls, towering firs, and carefully planned gardens creates an atmosphere of tranquility that feels far removed from the nearby city.

Whether seeking spiritual reflection or simply a peaceful afternoon, The Grotto offers a unique blend of artistic beauty and natural serenity that makes it one of Portland’s most treasured spaces.

Beyond the Tourist Trail: Portland’s True Character

Portland’s charm lies not in grand tourist attractions, but in these offbeat experiences that reveal the city’s true personality.

From soaking in a floating hot tub on the Willamette to discovering tiny art installations along neighborhood sidewalks, these unconventional activities showcase Portland’s creative spirit and community-driven culture.

Each experience tells a different story about the city. The Peculiarium celebrates Portland’s love of the weird, while Mill Ends Park demonstrates how the city transforms even the smallest spaces into sources of joy.

The Witch’s Castle and Zymoglyphic Museum reveal Portland’s appreciation for both natural and artistic beauty, while Powell’s Books stands as a testament to the city’s intellectual curiosity and independent spirit.

These attractions offer something for everyone – families can enjoy Shakespeare in the park or hunt for sidewalk art, couples can find romance at The Grotto, and adventure seekers can explore Forest Park’s hidden treasures.

Consider these suggestions not just as items on a checklist, but as gateways to understanding why Portland proudly keeps itself weird, wonderful, and welcoming to all who wish to explore its unique offerings.

FAQs about Things to Do in Portland

From hidden waterfalls to floating hot tubs, Portland offers endless possibilities for adventure. Here are answers to your most common questions about exploring the Rose City: