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 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!
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!
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.
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.
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 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 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
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 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.
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
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.
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
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.