Three Nerdy Days in Portland

Portland is Nerdy by Nature, so we put together the perfect 3 day itinerary to Nerd Out for the ultimate long Geek Weekend.

Day 1: High Fantasy, Mossy Ruins, and Haunted Elixirs

You touch down in the Rose City and make a direct line for the Central Eastside, pulling into the Jupiter Hotel. This midcentury motor inn-turned-stylish boutique refuge serves as your retro-cool urban base camp.

9:00 AM – You fuel up on custom pour-overs and whimsical pastries at Wonderwood Springs, a coffee shop meticulously crafted by a local artist to look like a living, hand-drawn medieval fantasy kingdom.

11:30 AM – You head west into the dense, emerald canopy of Forest Park. Following the Lower Macleay Trail, you embark on a short, moss-draped hike alongside Balch Creek until the forest parts to reveal the Witch's Castle. You spend an hour exploring these roofless, haunting WPA-era stone ruins, absorbing the eerie local folklore that permanently clings to the mossy basalt walls.

3:00 PM – Back downtown, you lose yourself inside the towering, multi-story labyrinth of Powell's City of Books, the largest independent used and new bookstore in the world. You wander through miles of color-coded aisles, hunting for rare sci-fi paperbacks and obscure graphic novels.

7:30 PM – Dinner is a theatrical descent into the macabre at Raven's Manor, a gothic, mad-scientist-themed restaurant / bar. You feast on upscale gastropub fare while a "potion master" guides you through a mix-your-own elixir experience, complete with smoking test tubes and color-changing liquors.

11:00pm - Finish out your Friday night by time warping to the longest continuously running of the Rocky Horror Picture Show at the Clinton Street Theater.  Most screenings include a guest host, performance or shadow cast of the Clinton Street Cabaret.*

Day 2: Submarines, Pinball Wizards, and Retro Gaming

You wake up early on the Eastside and grab a quick, artisanal bite across the street at Grendel’s Coffee House before walking down to the riverfront.

10:00 AM – You spend your morning diving into the massive, industrial halls of the Oregon Museum of Science and Industry (OMSI). After testing your skills in the physics and chemistry labs, you head outside to the Willamette River docks for an intimate tour of the USS Blueback, a real, decommissioned Navy submarine parked right in the water.

2:00 PM – Lunch is casual food cart fare at the Wonderlove Food Cart Pod, followed by a quick ten-minute walk from your hotel to Hopscotch Portland, an expansive, experiential indoor art playground packed with interactive light arrays, responsive trampolines, and mind-bending digital installations.

8:00 PM – As night falls, you head into Old Town for a pilgrimage to Ground Kontrol Classic Arcade, a legendary, two-story monument to vintage gaming. Beneath glowing neon accents, you sip a uniquely themed cocktail while pumping tokens into immaculately restored 1980s arcade cabinets and a massive wall of classic pinball machines.

Day 3: Tabletop Lore, Middle-earth, and Late-Night Quests

You kick off your final day by exploring Portland's deep-rooted tabletop and fantasy subcultures.

11:00 AM – You grab brunch at TPK Brewing, a fantasy-themed cafe where you can sip your morning brew surrounded by medieval shields, custom terrain maps, and local lore.

1:00 PM – You spend the afternoon at Guardian Games, a colossal, warehouse-sized haven for geeks. You browse thousands of board games, miniatures, and dice bags, eventually wandering to the back of the store to grab a local craft draft at Critical Sip, their in-house, over-21 board game bar.

6:30 PM – You wrap up your long weekend by traveling to the cozy confines of The Paladin’s League for fresh grub and gaming, enjoy hand crafted cocktails and a fully stocked soda fountain as you toast to a perfect, beautifully nerdy 72 hours.