Since we were already planning a trip to visit family on the Oregon Coast, we decided to squeeze in a few days in Portland—a city that holds a special place in both of our hearts. We each lived in Portland at different times before we met, so it was fun getting to experience the city together and revisit some of our favorite spots. Portland is one of those places that instantly charms you with its beautiful old homes, walkable neighborhoods, towering trees, and endless green spaces. We love it so much that if housing prices weren’t still a bit out of reach, we would seriously consider moving there someday.

What To Do

Cathedral Park

Our first stop after arriving in Portland from the Oregon Coast was Cathedral Park in the St. Johns neighborhood. This park is especially meaningful to us because Andrew lived in St. Johns for several years and used to visit regularly with his Portuguese Water Dog, Arlo. Cathedral Park sits beneath the iconic St. Johns Bridge, widely considered one of the most beautiful bridges in Portland thanks to its soaring Gothic-inspired towers and dramatic architecture. Unfortunately, part of the park was under construction during our visit, but we still enjoyed taking in the unique perspective of the bridge from below and reminiscing about Andrew’s time in the neighborhood.

Forest Park

After grabbing coffee and lunch at Sparrow Bakery, where Andrew used to work, we headed over to Forest Park for a hike. Covering more than 5,000 acres, Forest Park is one of the largest urban forests in the United States and contains over 80 miles of trails winding through lush Pacific Northwest scenery. One of the park’s entrances is located just across the river from St. Johns, making it a favorite destination for Andrew and Arlo’s daily walks when he lived nearby. We opted for a short, easy trail that allowed us to stretch our legs and enjoy the peaceful forest before checking into our downtown hotel.

International Rose Test Garden

The next morning, after enjoying breakfast via room service, we made our way to the International Rose Test Garden. This was always one of my favorite places when I lived in Portland, and returning reminded me exactly why. Located in Washington Park, the garden features thousands of rose bushes representing hundreds of varieties from around the world, along with stunning panoramic views of downtown Portland and, on clear days, Mount Hood. We spent time strolling the pathways with Arlo and our toddler, Sage, soaking in the fragrant blooms and picturesque scenery that make this spot feel truly magical.

Laurelhurst Park

Later that day, we found ourselves in the Laurelhurst neighborhood while driving around and admiring houses during Sage’s nap. Once he woke up, we stopped at Laurelhurst Park so everyone could get out and stretch their legs. This beloved neighborhood park is known for its winding pathways, large pond, mature trees, and wide-open lawns that draw locals throughout the year. It’s the kind of place where you’ll find people reading under shady trees, enjoying picnics, sunbathing on the grass, or simply relaxing with friends, and it perfectly captures Portland’s laid-back outdoor lifestyle.

Exploring Portland’s Neighborhoods

One of the things we love most about Portland is its collection of distinct neighborhoods, each with its own personality, local restaurants, coffee shops, boutiques, and community feel. During this trip, we spent time exploring some of our favorites, including the Alberta Arts District, Mississippi Avenue, and the Burnside/Laurelhurst area. Alberta is known for its colorful murals, creative energy, and independent businesses, while Mississippi offers a fun mix of trendy restaurants, vintage shops, and neighborhood charm. Although a lot has changed since we both lived in Portland, it was comforting to see many of the familiar places we remembered still standing alongside the city’s newer additions.

Where To Eat

Arden

Our first night in Portland set the bar incredibly high. Dinner at Arden ended up being our favorite restaurant experience of the entire trip. As a chef and former restaurant industry professional, Andrew is always paying close attention to the details, and he was genuinely impressed by both the food and the team. Every dish felt thoughtful and beautifully executed, and the service struck that perfect balance of professionalism and warmth. From start to finish, the experience felt special without being pretentious. If we could only recommend one restaurant from our trip, Arden would be it.

Coava Coffee

The next morning, we started our day with coffee and pastries at Coava Coffee Roasters. This has long been one of my favorite coffee shops in Portland, and their honey latte remains one of my favorite coffee drinks anywhere. Beyond the coffee itself, I love the atmosphere. The industrial space feels distinctly Portland—modern, creative, and effortlessly cool. It was the perfect place to ease into our first full day in the city before heading out to explore.

Terra Mae

That evening, we had dinner at Terra Mae, and the restaurant was absolutely stunning. The interior design immediately caught our attention, with lush plants and beautiful details creating a warm, inviting atmosphere. The concept is equally impressive: a woman-led team serving a creative blend of Portuguese and Japanese cuisine. Every dish felt unique and thoughtfully crafted, showcasing flavors and combinations we hadn’t experienced before. Terra Mae manages to feel both elegant and approachable, making it a standout dining destination in Portland.

Upper Left Roasters

On our final morning, we headed to Upper Left Roasters for brunch before leaving the city. This was Andrew’s favorite coffee of the trip, and it’s easy to see why. The coffee was excellent, but the food was equally memorable—especially their incredible toasts. The café has a lively energy, filled with people working remotely, catching up with friends, or simply enjoying a great cup of coffee and breakfast. It’s the kind of neighborhood spot that makes you wish you lived nearby.

Where To Shop

Pistils Nursery

One of our first stops was the Mississippi neighborhood, which has always been one of our favorite areas in Portland. While exploring, we visited Pistils Nursery, a plant shop that feels like a dream for fellow plant lovers. My husband and I both love plants, so we could easily spend hours browsing the beautiful houseplants, unique pots, and endless greenery that fill the space.

Goodbye Horses Vintage

Later that afternoon, we were driving through the Laurelhurst neighborhood while Sage napped in the car when I spotted Goodbye Horses and asked my husband if I could jump out to take a look. The vintage shop was full of cute, well-curated pieces at surprisingly reasonable prices. I even met one of the owners and learned that the shop is named after the song “Goodbye Horses” from The Silence of the Lambs soundtrack, which made us laugh because it had been on our road trip playlist earlier that day.

Zig Zag Vintage

At the end of the day, we found ourselves in the Alberta Arts District waiting for our reservation at Terra Mae and stopped into Zig Zag Vintage. It was actually a shop I used to visit when I lived in Portland in 2019, so it was fun to see it still thriving years later. Like Goodbye Horses, the shop had a great selection of vintage clothing at reasonable prices, plus an adorable shop dog who immediately gravitated toward my husband, Andrew.

Where To Stay

Kimpton Hotel Vintage

Our stay at Kimpton Hotel Vintage Portland was the perfect blend of style, comfort, and convenience for our family. Located in the heart of downtown Portland, the hotel made exploring the city easy while providing a cozy retreat at the end of each day. We loved the wine-inspired theme woven throughout the property, especially the evening wine tasting hour, and appreciated how spacious and comfortable our room was for traveling with both a toddler and our dog. The staff were incredibly welcoming, the valet service was quick and efficient, and the dining options were excellent—from breakfast at Il Solito and a relaxing room service breakfast to cocktails and dinner at Bacchus Bar. With its pet-friendly accommodations, thoughtful amenities, welcoming atmosphere, and unbeatable location, Kimpton Hotel Vintage Portland delivered a memorable family getaway and is a place we would gladly stay again.

Even though our time in Portland was short, it reminded us why we fell in love with the city in the first place. Between the beautiful parks, charming neighborhoods, incredible food, and endless outdoor spaces, Portland offers something special around every corner. Sharing these places with Sage and revisiting old memories together made this trip especially meaningful. We left feeling nostalgic, inspired, and already looking forward to our next visit.

XOXO