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leaves

Things To DoThings To Do

September is a good time to visit Portland and Oregon. The weather is usually mildly humid but cool, with temperatures ranging from 52—77°F (11—25°C). There are plenty of events to check out and activities to try during this time in Portland and in Oregon. Here are some of our top favorite recommendations...
Spirit Of Halloweentown

Spirit Of HalloweentownSpirit Of Halloweentown

275 Strand Street, St. Helens, OR 97051

Do you remember the 1998 Disney classic Halloweentown? Believe it or not, the movie was filmed right here in Oregon—in the heart of St. Helens, just about an hour from Portland. Each year, the town transforms into “Spirit of Halloweentown,” a month-long celebration that typically runs from late September through Halloween, complete with the iconic pumpkin, spooky decorations, photo ops, and themed events. St. Helens is also known for filming scenes from the first Twilight movie, making it a fun stop for movie lovers. If you're looking for a festive fall adventure, be sure to plan a visit and experience the magic for yourself.

OMSI

OMSIOMSI

1945 Southeast Water Avenue, Portland, OR 97214

OMSI has always been one of our favorite places to explore. From immersive events like LEGO World to stunning Van Gogh exhibits and even catching a film in their incredible theater. There’s always something exciting happening. It’s a perfect spot for a fun date night or an afternoon adventure. Just be sure to check their website to see what events will be happening during your stay!

Wallace Books

Wallace BooksWallace Books

7241 Southeast Milwaukie Avenue, Portland, OR 97202

Jodi’s favorite! Wallace Books is located in the heart of Portland’s Sellwood/Westmoreland neighborhood is a must-visit for book lovers. This cozy shop is packed with new and used books, from the latest bestsellers to quirky, hard-to-find out-of-print treasures. When Jodi wants books, this is the place she goes. So, if you’re visiting Portland, make sure to stop by and browse the shelves!

Movie Madness Video

Movie Madness VideoMovie Madness Video

4320 Southeast Belmont Street, Portland, OR 97215

William’s favorite! If you miss Blockbuster or just want to step back into the ’90s and experience a real video rental store, you have to check out Movie Madness. Founded in 1991 by Mike Clark, this legendary Portland spot has grown to house more than 90,000 titles. Now a nonprofit run by the Hollywood Theatre, Movie Madness is loved for its enormous film collection, its staff of true movie experts, and its incredible display cases filled with authentic film props and costumes from across movie history. If you’re visiting Portland and you’re even a little bit of a film fan, this place is an absolute must-visit.

McMenamins Crystal Ballroom

McMenamins Crystal BallroomMcMenamins Crystal Ballroom

1332 West Burnside Street, Portland, OR 97209

Our Favorite! After you finish exploring Powell’s City of Books, take a short walk—just a few minutes—and treat yourself to a drink or a bite at McMenamins. This Portland classic has a cozy, eclectic atmosphere, colorful artwork, and the laid-back vibe the McMenamins pubs are known for. It’s the perfect spot to unwind with a craft beer, cocktail, or hearty pub fare after browsing books. If you’re visiting Portland, don’t miss the chance to stop in and experience one of the city’s most iconic local hangouts just steps from Powell’s.

Astoria

AstoriaAstoria

Astoria, OR 97103

Looking to escape Portland for a bit? Head to Astoria. Just two hours away, it's an inviting coastal town where the Columbia River meets the Pacific Ocean. Visitors can enjoy stunning views from the Astoria Column, explore maritime history at local museums, stroll the scenic riverwalk, and visit famous filming spots from The Goonies. With fresh seafood, craft breweries, and charming Victorian architecture, Astoria offers the perfect mix of relaxation, adventure, and small-town character.

Powell's City of Books

Powell's City of BooksPowell's City of Books

1005 West Burnside Street, Portland, OR 97209

Powell's is more than a famous Portland landmark — it’s the world’s largest independent bookstore, and it’s a microcosm of Portland, packed with smart and eclectic offerings and passionate people. Spanning an entire city block, Powell’s City of Books boasts a collection of more than 1 million new and used books, plus an excellent array of housewares, games, greeting cards and more. Whether you’re searching for an out-of-print indie novella, an inclusive new tarot deck or the latest romance bestseller, this iconic bookstore has it all.

Hopscotch Portland

Hopscotch PortlandHopscotch Portland

1020 Southeast 10th Avenue, Portland, OR 97214

Hopscotch is a theme park of immersive art exhibits that further enhances the city’s creative culture. Akin to art attractions like Meow Wolf and TeamLab, Hopscotch is a 23,000-square-foot (7,010 sq m) multi-room gallery in Southeast Portland’s Central Eastside. Upon entering, you can disconnect, relax and appreciate the team’s collection of stimulating visual, auditory and sensory pieces

Raven's Manor

Raven's ManorRaven's Manor

235 Southwest 1st Avenue, Portland, OR 97204

If you’re looking for something different in Portland, stop by Raven’s Manor. It’s a haunted-house style cocktail bar right downtown—dark, theatrical, and perfect if you’re into themed drinks or cool photo spots. It’s a great place to start a night out.

Glowing Greens Indoor Mini-Golf

Glowing Greens Indoor Mini-GolfGlowing Greens Indoor Mini-Golf

509 Southwest Taylor Street, Portland, OR 97204

Glowing Greens Indoor Mini-Golf in Portland is a black-light, glow-in-the-dark mini-golf course that’s fun and easy for the whole family. The bright neon artwork, pirate-themed rooms, and 3-D effects make it feel like a mini adventure instead of a standard golf game. Because it’s indoors, it’s a perfect family activity no matter the weather, and the course is simple enough for young kids while still entertaining for teens and adults. This place also have axe throwing and escape rooms.

Next Level Pinball Shop & Museum

Next Level Pinball Shop & MuseumNext Level Pinball Shop & Museum

1458 NE 25th Ave, Hillsboro, OR 97214

Have kids? No worries at all! If you’re up for a short drive (about 30 minutes outside of Portland), Next Level Pinball Shop & Museum in Hillsboro is a fantastic family-friendly option. With hundreds of arcade and pinball games set to free play with one admission, plus colorful pop-culture displays that feel like a museum kids can explore, there’s something for everyone. Games for all ages, plenty of room to move around, and an all-day pass make it an easy, fun indoor activity—especially on a classic rainy Portland day

Multnomah Falls

Multnomah FallsMultnomah Falls

OR 97014

One of Oregon’s most stunning natural landmarks—a 620-foot, two-tier waterfall that you can admire up close without a long hike. With its dramatic cliffs, lush green forest, and the iconic Benson Bridge offering a breathtaking viewpoint, the falls feel both powerful and peaceful. It’s an easy, unforgettable stop where nature’s beauty is on full display, making it a must-see for any trip to Portland or while you are in Portland.

Pittock Mansion

Pittock MansionPittock Mansion

3229 Northwest Pittock Drive, Portland, OR 97210

For a perfect blend of Portland history and jaw-dropping views, head up to Pittock Mansion. Perched above the city, it offers incredible photo ops, forested trails, and a glimpse into the life of one of Portland’s founding families

Forest Park

Forest ParkForest Park

4099 NW Thurman St, Portland, OR 97210

If you’re into hiking, Forest Park is a must. It’s one of the largest urban forests in the country, with tons of trails—everything from easy walks to longer, more rugged routes

Portland Japanese Garden

Portland Japanese GardenPortland Japanese Garden

611 Southwest Kingston Avenue, Portland, OR 97205

The Portland Japanese Garden is one of the most peaceful and beautiful places in the city. It’s designed to look like a traditional Japanese garden, with winding paths, koi ponds, waterfalls, and perfectly manicured plants. Many people say it’s the most authentic Japanese garden outside of Japan. It’s a great place for visitors to relax, enjoy nature, take photos, and experience a sense of calm right in the middle of Portland. Families, couples, and solo travelers all love it for the scenery and the quiet atmosphere.