I’m all about getting away from the crowds, so this post is long overdue.

Portland is a city that thrives on individuality and creativity. Unlike other major cities, Portland prides itself on its eclectic neighborhoods, vibrant arts scene, and a commitment to sustainability. Not to mention, it’s one of the top foodie cities in the country. The city’s unofficial motto, “Keep Portland Weird,” is a testament to its embrace of the unconventional and the offbeat. It’s why I lived there for over 20 years.

If you’re seeking experiences beyond the typical tourist attractions, Portland offers a ton of local favorites that capture the city’s distinctive spirit. This 3-day itinerary is designed to guide you through some of Portland’s lesser-known treasures, providing an authentic taste of what makes this city truly special.

These spots are all perfect for travelers who want to dive deeper into Portland’s eccentric soul. Whether you’re into art, history, oddities, or just peaceful nature away from the tourist drag, these stops will leave you with quirky stories and Instagram-worthy photos.

Itinerary for Portland, Oregon

If you’d like a more personalized itinerary (anywhere), I can help. I am a certified travel planner and can book a trip tailor-made for you and your unique desires – all that fits within your budget. Read more!

Day 1: Exploring Northeast Portland’s Treasures

Morning: Breakfast at Pine State Biscuits

• Location: 2204 NE Alberta St, Portland, OR 97211
• Why Visit: A local favorite known for its hearty, Southern-inspired breakfast fare.
• Unique Feature: Their signature biscuits are made from scratch and have garnered a cult following.
• Website: Pine State Biscuits

Late Morning: The Grotto – National Sanctuary of Our Sorrowful Mother

• Location: 8840 NE Skidmore St, Portland, OR 97220
• Why Visit: A serene 62-acre Catholic shrine and botanical garden offering a peaceful retreat from the city bustle.
• Admission: Upper-level gardens: $8.00 for adults.
• Unique Feature: Features a cliffside meditation chapel with panoramic views of the Columbia River Valley.

Lunch: Güero

• Location: 200 NE 28th Ave, Portland, OR 97232
• Why Visit: A vibrant spot offering tortas and other Mexican street food with a modern twist.
• Unique Feature: Their “Ahogada” torta is a must-try, featuring pork carnitas in a spicy tomato sauce.
• Website: Güero

Afternoon: Alberta Arts District

• Location: NE Alberta St, Portland, OR
• Why Visit: A culturally rich neighborhood filled with colorful murals, indie boutiques, and art galleries.
• Unique Feature: The district hosts a Last Thursday art walk, showcasing local artists and performers.

Read my post about the Albert Arts District!

Dinner: Expatriate

• Location: 5424 NE 30th Ave, Portland, OR 97211
• Why Visit: A chic lounge offering inventive Asian-inspired small plates and cocktails.
• Unique Feature: Owned by a James Beard Award-winning chef, the menu is both adventurous and accessible.
• Website: Expatriate

Day 2: South Portland and Nature Escapes

Morning: Breakfast at Coquine

• Location: 6839 SE Belmont St, Portland, OR 97215
• Why Visit: A cozy neighborhood restaurant known for its seasonal, locally sourced breakfast offerings.
• Unique Feature: Their house-made pastries and granola are standout items.
• Website: Coquine

Late Morning: Tryon Creek State Natural Area

• Location: 11321 SW Terwilliger Blvd, Portland, OR 97219
• Why Visit: A lush forested park offering miles of hiking and equestrian trails.
• Unique Feature: It’s the only Oregon state park within a major metropolitan area.

Lunch: Bamboo Grove Hawaiian Grille

• Location: 51 SW 3rd Ave, Portland, OR 97204
• Why Visit: A laid-back spot serving authentic Hawaiian plate lunches.
• Unique Feature: Known for their Kalua pig and macaroni salad.
• Website: Bamboo Grove

Afternoon: Crystal Springs Rhododendron Garden

• Location: 5801 SE 28th Ave, Portland, OR 97202
• Why Visit: A 9.5-acre garden featuring an extensive collection of rhododendrons and azaleas.
• Admission: $5.00 for adults during peak season.
• Unique Feature: The garden’s tranquil setting includes waterfalls and picturesque bridges.(Explorial)

Dinner: Jacqueline

• Location: 2039 SE Clinton St, Portland, OR 97202
• Why Visit: A seafood-centric restaurant with a whimsical atmosphere.
• Unique Feature: Offers a rotating selection of fresh oysters and seafood dishes.
• Website: Jacqueline

Day 3: Westside Wonders and Forest Trails

Morning: Breakfast at Ken’s Artisan Bakery

• Location: 338 NW 21st Ave, Portland, OR 97209
• Why Visit: A beloved bakery known for its European-style breads and pastries.
• Unique Feature: Their croissants and morning buns are my favorite in the city.
• Website: Ken’s Artisan Bakery

Late Morning: Forest Park – Wildwood Trail

• Location: Access via NW 29th Ave & Upshur St, Portland, OR 97210
• Why Visit: One of the largest urban forests in the U.S., my favorite park in the city by far, offering over 80 miles of trails.The Wildwood Trail provides a serene escape with lush greenery and wildlife sightings.

Lunch: Ataula

• Location: 1818 NW 23rd Pl, Portland, OR 97210
• Why Visit: A modern Spanish tapas restaurant offering a vibrant dining experience.
• Unique Feature: Their paella and sangria are standout menu items.
• Website: Ataula

Afternoon: Pittock Mansion

• Location: 3229 NW Pittock Dr, Portland, OR 97210
• Why Visit: A historic mansion offering panoramic views of Portland and Mount Hood.
• Admission: $12.00 for adults.
• Unique Feature: The mansion’s architecture and period furnishings provide a glimpse into early 20th-century Portland life.
• Website: Pittock Mansion

Dinner: Canard

• Location: 734 E Burnside St, Portland, OR 97214
• Why Visit: Canard is the more playful, less pricey sibling of Le Pigeon (right next door)—owned by the same chef, Gabriel Rucker. It serves inventive small plates that blend French technique with American creativity.
• Unique Feature: Their steam burger is legendary (think elevated White Castle), and the menu includes clever dishes like foie gras dumplings and duck stack pancakes.
• Atmosphere: Hip, lively, and perfect for sharing a few small plates without breaking the bank.
• Website: canardpdx.com

Pro Tip: If you’re set on French cuisine but want something even more casual and neighborhood-y, try:

Berlu

• Location: 605 SE Belmont St, Portland, OR 97214
• Why Visit: A modern Vietnamese bakery by day and an affordable fine-dining-style tasting menu experience by night (weekends only). Their pastries are gorgeous and they occasionally offer walk-in dinners with a fixed, reasonable price.
• Website: berlupdx.com

Here are 5 more off-the-beaten-path places and attractions in Portland, Oregon (or within 20 miles) to swap into your itinerary. Each offers a unique experience that even many locals haven’t fully discovered.

Witch’s Castle (Stone House) in Forest Park

• Location: Lower Macleay Trail, starting at NW 29th Ave & Upshur St, Portland, OR 97210
• Why Visit: A moss-covered, abandoned stone structure hidden in Forest Park that feels like a scene from a fairytale.
• Unique Feature: It’s rumored to be haunted and has a spooky local legend attached. The short 0.8-mile hike to get there adds to the mystery.
• Pro Tip: Go early in the morning to avoid crowds and catch the soft forest light through the trees.

Mill Ends Park (World’s Smallest Park)

• Location: SW Naito Parkway & Taylor Street, Portland, OR 97204
• Why Visit: It’s officially recognized by the Guinness Book of World Records as the smallest park in the world—only 2 feet in diameter!
• Unique Feature: This quirky attraction embodies Portland’s sense of humor and creative urban planning.
• Pro Tip: It’s a quick visit, so combine it with a walk along the waterfront or nearby Tom McCall Waterfront Park.

Zymoglyphic Museum

• Location: 6225 SE Alder St, Portland, OR 97215 (open by appointment)
• Why Visit: A fascinating cabinet of curiosities featuring strange art made from natural objects, found items, and obscure artifacts.
• Admission: Donation-based; contact the museum to schedule a visit.
• Unique Feature: It’s one person’s lifelong art installation, dedicated to the “Zymoglyphic” aesthetic—half science fiction, half Victorian oddities.
• Website: zymoglyphic.org
• Pro Tip: This is truly obscure—perfect for lovers of art, taxidermy, and the bizarre.

Sauvie Island’s Warrior Rock Lighthouse

• Location: Start at Warrior Point Trailhead on Sauvie Island, about 18 miles from downtown Portland
• Why Visit: A scenic 3-mile (one-way) hike along the Columbia River to Oregon’s smallest lighthouse. You’ll need a Sauvie Island parking permit ($10 daily / $30 annual). You’ll feel miles away from the city on this quiet riverside trail, often accompanied by bald eagle sightings.
• Pro Tip: Visit during the week for fewer people and a peaceful lighthouse photo op.

Velveteria: The Museum of Velvet Paintings

• Location: 511 NE 23rd Ave, Portland, OR 97232
• Why Visit: A niche museum dedicated entirely to the misunderstood art of black velvet painting.
• Admission: $10 for adults (cash only)
• Unique Feature: Elvis, unicorns, skeletons, and a whole room of erotic velvet art. It’s hilarious, weird, and oddly touching.
• Website: velveteria.com
• Pro Tip: The owners love to give personal tours—ask about their favorite pieces.

Want more? Read 17 Unusual Things to Do in Portland.