A Day in Old Town Portland: Must-Visit Attractions and Eateries

Ever wondered if there exists a place where you can find a flawless fusion of history, culture, and incredible food? Then look no further than Old Town Portland. This historic neighbourhood of the “city of roses” provides a lovely mix of quirky charm, fascinating history, and flavourful mouth-watering eats . You will find a unique one-of-a-kind experience where history-meets-modernism. Whether you’re a history buff, a foodie, or just someone who loves exploring new places, this is a destination your heart is craving for. 

Old Town Portland offers you more than just your typical tourist attractions or trendy spots. It's a vibrant neighborhood full of hidden gems that are waiting to be explored. It is the place where history, culture and culinary delights all come together in the best way possible.  And what in fact will make you fall in love with this city is how it welcomes its visitors. Full of warmth, this city is always open to all. So book your tickets now and come visit to give your busy days a wholesome treat. 

Need a guide for the whereabouts? How to start? Where to start? Do not worry! This blog is here to guide you to the must-see spots and can’t-miss eateries that promise to make your visit worthy. Here is the ultimate itinerary for a day in Old Town that will help you explore the best of the city.


Morning Exploration

The morning hours are just perfect for soaking in the city’s rich heritage. The charm of local artisans of the Saturday Market will effortlessly etch a special space in your memory and the Chinese garden will surely help you have a relaxing start to your morning. Here is where you can commence the matchless morning exploration in Old Town:


Portland Saturday Market : The market showcases a wide variety of handmade goods, all crafted by the local artisans. It is bursting with local crafts, art, and food vendors from the Pacific Northwest. And you can often meet the artists whose creations are up for sale. It flourishes itself as a central economic engine for the historic Old Town Portland. You will surely meet local artisans and if you are lucky, maybe even find that perfect quirky souvenir. Plus, there’s usually live music to give your day a good start.

a bright sunny day, clear skies and stalls selling food and other items with lots of people

Lan Su Chinese GardenAn authentic Chinese garden, Lan Su serves as a serene oasis in the middle of the city. Also titled as the Garden of Awakening Orchids, the garden is beautifully decorated with traditional Chinese architecture. It is a lovely spot to relax and ease your mind.  Lan Su Chinese Garden serves as a bridge of connection between the cultures of the home city, Portland, Oregon and Suzhou, China while at the same time offering an ethereal experience. While strolling through the serene scenery with tea houses and cultural events, you can treat yourself with traditional Chinese dishes such as wonton soup and “congee of the day” as well as Chinese pastries and donuts from Mei Sum and Heyday Donuts. What can be more refreshing than a walk in the garden to serve as a break from the humdrum and busy schedule of city life? 

Spending a Leisurely Afternoon in Portland

 As the morning gives way to midday, Old Town Portland does not give away its buzz of excitement and possibilities. This is the time when you can dive into some of the neighbourhood’s timeless attractions and indulge in its culinary delights. The Maritime Museum takes you back to maritime history and Pioneer Courthouse Square offers you a “living room”. Old Town Pizza & Brewing gets you craft brew delights and the awesome Charlie’s Deli renders the ultimate charisma of Portland foods.  Here is how to make the most of your midday adventure in Old Town:

Oregon Maritime Museum : Experience the life of adventure on the river once you come to Old Town Portland. Located on the Willamette River, Oregon Maritime Museum is a historic steam-powered tugboat. Apart from exhibiting on Portland’s maritime history, the museum attracts a lot of ship model enthusiasts and researchers offering an array of photographs related to maritime history in the Northwest region.  The artefacts that are kept for demonstration on the cabin deck, represent a small fraction of the deep-rooted history of the working river in the Portland region. Your inquisitive mind will thank you for the views of the Willamette River that are nothing but fantastic.

a ferry docked in a river

Pioneer Courthouse Square : In the heart of downtown Portland, Pioneer Courthouse Square serves as the city’s central urban park. Known as Portland’s living room, it hosts numerous public events and gatherings giving way to fostering community connections. With over 300 events annually, the Square is a hub for residents and visitors, while at the same time offering an informal gathering space so that everyone can feel at home. Whether you are setting your foot in Portland for the first time or you have been here for years, Pioneer Courthouse Square is the ultimate place to get oriented and experience the real essence of the city. 

an outdoor patio area with lots of steps leading down to a stage area surrounding by buildings

Lunch at Charlie’s Deli : Situated in the heart of Portland, Charlie’s Deli is the perfect cozy spot to relax and feel right at home. Whether it is Portland sandwiches that you’re craving for or a Pastrami, Charlie’s Deli and its cozy and welcoming atmosphere is the ultimate place where you can find everything. Do stop second guessing if you are a wellness enthusiast or health nut, and let your tummy rumble for its delicious culinaries. Because Charlie’s Deli offers a number of options for health-conscious choices including gluten free breads, salads, fresh and colourful veggies and whatnot. Being a family-owned deli with a focus on fresh ingredients, you can depend on it for your lunchtime cravings. Alicia’s Cuban Sandwich, Prime Rib Philly, The Italian Job, Real Turkey on Ciabatta and many more dishes are the ones waiting to appease your appetite. Nothing can beat the crunch of fresh, organic, juicy and lively vegetables – a staple in Portland sandwiches. From tomato to lettuce, onion to cucumber, black olives to pepperoncini and French dijon mustard – they not only bring vibrant colours but also add flavours to every bite.

The cashier register at Charlies Deli. sandwiches are being served to happy customers


Onto sightseeing activities

After lunch indulge in leisurely sightseeing. Fathom out the historic Shanghai Tunnel and smell the celebration of art at the Art Museum.  Hey bibliophiles, have a great advantage of the afternoon sightseeing at Powell’s City of Books! 

Portland Underground (Shanghai Tunnels): Wander over to the historic tunnels - Shanghai Tunnels, also known as the Portland Underground as a treat to your after-lunch self. This tunnel is a network of passages in Portland, Oregon, primarily located beneath the Old Town neighbourhood which extends to the main business district. These tunnels were created to link the basements of numerous hotels and taverns to the Willamette River waterfront. Though originally constructed to transport goods from docked ships to basement storage areas for enabling businesses to bypass streetcar and train traffic for more efficient deliveries, back in the days, these tunnels were used for all sorts of illicit activities - from smuggling to, well, less savoury business. But worry not, today you can take a tour through this tunnel and learn about these fascinating (and slightly spooky) stories of Portland’s underground history.  

Portland Art Museum:  Pardon the dust of Portland Art Museum, the vibrant cultural hub because it showcases a variety of art centres including those dedicated to Native American art, Northwest art, and modern and contemporary art as well. It also offers permanent exhibitions of Asian art and an outdoor public sculpture garden.  It is an offering of a rich and extensive collection of art to experience, whether you are an art enthusiast and casual visitor. Special exhibits and events include Pissarro to Picasso: Masterworks on Loan from the Kirkland Family Collection, Monet to Matisse: French Moderns and many more. Head to the PAM and cherish the best! 

Powell’s City of Book: Powell’s headquarters that is also dubbed Powell’s City of Books, claims to be the World’s largest independent bookstore where you can find both new and used books throughout the world. And believe it or not you will never get bored here.  There are shelves that shelf new and used versions of each book together, so there are different price options as well. Their collection of rare books also garner a lot of attention. New and used books effortlessly find space across multiple floors here. Truly satisfying for a book lover! 

a corner bookstore with new and used books

Ending the day in peace

 As the afternoon slides away and the evening rolls into, it is time to find a good spot for happy hour. Let’s enliven the vigour of your spirit as the day comes to end. With the setting of the sun, get the sight of the city's beauty from the Cruises. Wrap up your day with a refreshing change of pace and give your tired nerves a chance to unwind.

Portland Spirit Cruises:  Evenings are the perfect time to head to the Portland Spirit Cruises that offer a unique way to explore Portland. You can embark on a scenic cruise along the Willamette and Columbia Rivers, where you can enjoy stunning views of the city’s beauties - skyline, bridges, and natural beauty and everything you want. The cruises range from relaxing daytime tours to elegant dinner cruises, complete with gourmet meals and live entertainment. It is nothing but perfect for a romantic evening or a fun outing with friends. Portland Spirit Cruises promise to provide a memorable experience to remain highlighted with the charm and beauty of the Pacific Northwest. 

A spirit cruise in the middle of the river with beautiful trees in the background

There you are – a full day of adventure, history, delicious food, and good vibes all that Old Town Portland can offer. Whether you are exploring the markets for doughnuts or fresh traditional tea, diving into the local history of tunnels or museums or, having the best lunch ever or your bibliophile self-looking for ultimate solace, here the Old Town Portland has got something for everyone in this eclectic neighbourhood.  When it is a matter of having the heavenly dishes of Portland, Charlie’s Deli sandwiches and other foods are the testament to the city’s everlasting love for culinary innovation. No matter if you are a vegetarian or non vegetarian, it is ready to serve something to satisfy every craving. Want some innovative combination of classic and modern to surprise your taste buds?  Charlie’s Deli and other Old Town Portland eateries offer everything you are craving for. So, grab your walking shoes, book your ticket, bring your hunger for adventure (and for food obviously), and get ready to experience the best of Old Town Portland.