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Two people stand on benches in a forest with tall trees, arms outstretched and looking up, surrounded by greenery and sunlight filtering through the branches.

A Perfect Day in Portland: Brunch, Books, S’mores, and Stunning Views with Family

Abigail Toy

If you only have one day in Portland and want to pack it with the city’s best food, iconic sights, and local gems, here’s the itinerary we followed with our cousin who lives there. We started with brunch at Elephant’s Delicatessen, explored downtown shops including the Aesop store and Annex Bar, and then lost ourselves inside the legendary Powell’s Books. We treated ourselves at 1927 S’mores Company, drove up to Pittock Mansion for sweeping views and a walk among the Hoyt Arboretum redwoods, and made a sweet stop at Pie Spot while waiting for dinner at Luce, one of Portland’s coziest Italian restaurants. We ended the day at sunset with the breathtaking Multnomah Falls. Below is the full breakdown of how we fit it all in without feeling rushed, plus tips if you want to follow this route yourself.

At-a-Glance Portland Itinerary

  • Brunch: Elephant’s Delicatessen (gourmet food hall, amazing coffee and pastries)
  • Downtown Stroll: Aesop store + Annex Bar flat iron building
  • Book Lover’s Stop: Powell’s Books + in-store coffee room
  • Sweet Treat: 1927 S’mores Company (torch-fired gourmet s’mores)
  • Scenic Drive & Views: Pittock Mansion overlook + Hoyt Arboretum redwoods
  • Dessert Before Dinner: Pie Spot mini pies
  • Dinner: Luce (Italian comfort food)
  • Evening Finale: Multnomah Falls at sunset
Two people stand on benches in a forest with tall trees, arms outstretched and looking up, surrounded by greenery and sunlight filtering through the branches.

Elephants Delicatessen: A Gourmet Portland Icon

Our cousin suggested starting the day at Elephant’s Delicatessen, a Portland institution that blew us away from the moment we stepped inside. Imagine Cracker Barrel meets Whole Foods meets The Fresh Market meets Trader Joe’s, but in a distinctly authentic, local Portland way.

It is part gourmet food hall, part market, and part café, with made-from-scratch options, imported European specialties, gifts, and grab-and-go treats. We indulged in a savory egg bake, a perfectly soft blueberry muffin, and smooth lattes that reminded us why Portland is world-class when it comes to coffee.

Just when we thought we could not possibly eat more, our cousin insisted we try their chocolate mousse. She was right. It was rich, velvety, and worth every bite.

Spacious café interior with counters, display cases, and various seating areas. Customers and staff are visible, with food and drink stations throughout the space.
Plate with a slice of savory casserole and a blueberry muffin, next to a cup of latte with foam art and a blue PATH water bottle on a wooden table.

Downtown Stroll: Aesop Store & The Annex Bar

After brunch, we wandered through downtown Portland’s colorful streets. We unexpectedly came across an Aesop store, which was a fun surprise since I first discovered their luxurious hand soap in a Miami art museum bathroom. Yes, museum bathrooms can be life-changing. Outside, they had samples of their lotion, and I happily indulged.

Two people stand near a doorway, one dispensing liquid from a bottle onto the other’s hands. Trees and buildings are visible outside through the glass.

Nearby, we found The Annex Bar, a flat iron style building perched where West Burnside, SW Stark, and 12th Street meet. The area was alive with color and energy. It was a perfect snapshot of Portland’s charm and originality.

Three people are smiling while taking a selfie together outdoors on a city street with buildings and trees in the background.

Powell’s Books: The Largest Independent Bookstore in the World

If you visit Portland, Powell’s Books is non-negotiable. This multi-story wonderland has something for everyone, even those who do not read much. We started in the coffee room with cold brew for all. It is less acidic and easy on the stomach. Then we wandered between endless shelves.

We explored board games, pop culture treasures, and rare finds. Rich could not resist a book called How Technology Works, while my cousin and I picked up Cats of Japan prints as souvenirs.

We could have easily spent the entire day here, but other adventures were calling.

Three people smiling and posing for a selfie in the aisle of a bookstore with shelves filled with books in the background.
A man stands in a bookstore reading "How Technology Works," holding his chin thoughtfully. Shelves, signs, and other people are visible in the background.
Three people smile in a bookstore, holding copies of “Cats of Japan.” One person points to the book, displayed on a staff picks shelf behind them.
Two books, "Design Basics Made Easy" and "How Technology Works," are displayed upright on a wooden shelf in a bookstore with bookshelves in the background.
Books are displayed on a metal shelf, including titles about skateboards, management, life organization, and psychedelic reading.
A book cover featuring a distorted, screaming figure painting with "FRANCIS BACON" in large gold letters at the top.
A book titled "The Book of the Cat" featuring an illustration of a gray cat with green eyes lying down on the cover.
A book titled "The Golden Age of Advertising – the 60s" with a photo of a woman with a bob haircut and a white lace choker on the cover. Authored by Ed. Jim Heimann, published by Taschen.
A selection of hand lettering books displayed on a wooden bookshelf, with "The Hand Lettering Workbook" prominently featured in the center.
A bookshelf display labeled "Spaces + Places" featuring books about various cities and locations, including Italy, New York, London, Paris, and others, in a bookstore setting.
A bookstore display features nine fashion books arranged in a grid beneath a colorful "Pocket Fashion" sign on a wooden panel.
A wooden bookshelf with three shelves filled with books about color theory, color mixing, and related art topics, organized upright and stacked horizontally.
A wooden bookshelf in a bookstore filled with a variety of colorful books arranged vertically and horizontally on four shelves.
A gray Olivetti Underwood typewriter sits on a desk with a note reading, "Please Don't Play with Me, I'm Old and Delicate," placed in the paper holder.
A hanging sign labeled "CRAFTS" lists "doll collecting," "miniatures," and "toy collecting," with "929 pearl" at the bottom. A window with trees is in the background.
A pink book titled "How Not to Be a Hot Mess: A Survival Guide for Modern Life" by Craig & Devon Hase is displayed on a shelf among other books.
A blue book titled "The Tao of the Side Hustle" featuring an image of a person in martial arts attire holding a wooden staff.
A book titled "PIVOT: The Art and Science of Reinventing Your Career and Life" by Lisa Nichols is displayed on a shelf, featuring an illustration of a person turning a large arrow.
The cover of the book "The Practice: Shipping Creative Work" by Seth Godin, featuring concentric white circles on a blue background.
A shelf display of books including "In Case You Get Hit By a Bus," "The Psychedelic Reader," "Adaptogens," and "An Outsider’s Guide to Humans.
The book "Redesigning Work" by Lynda Gratton is displayed upright on a black wire shelf, showing a white cover with orange and purple geometric designs.
The cover of the book "Company of One" by Paul Jarvis, featuring small fish swimming left and one red fish swimming right, with the subtitle "Why staying small is the next big thing for business.
A package of Jean-Michel Basquiat magnetic bookmarks featuring three different artworks, displayed on a wooden shelf next to other Basquiat-themed items.

1927 S’mores Company: Gourmet Nostalgia

Next stop was 1927 S’mores Company, a torch-fired s’mores shop with an indoor and outdoor camping theme. S’mores have a special place in our hearts because they date back to the night Rich and I first met, so this was a must-visit.

We watched as the staff torched marshmallows in flavors like Marionberry, whiskey, and lemon. Our picks were:

  • Whiskey salted caramel, which was Rich’s favorite
  • Lemon poppyseed with blueberry compote, which was my favorite and also my cousin’s
  • Lemon Marionberry

Paired with drinks like meadow iced tea for us and a half caramel and half toasted marshmallow latte for Rich, it was pure happiness in dessert form.

A vintage lantern, three s'mores in paper trays, a "1927 S'mores Company" sign, a Girl Scout Handbook, and pinecones arranged on a rustic wooden shelf.

Pittock Mansion & Hoyt Arboretum Redwoods

With s’mores in our bellies, we drove our Mini Cooper through the scenic Arlington Heights neighborhood toward Pittock Mansion. The drive itself was stunning with lush trees, beautiful homes, and glimpses of nature everywhere.

The mansion’s overlook offered what Rich declared the best view of downtown Portland he has ever seen. Clouds kept Mt. Hood hidden, but it was still breathtaking. After soaking it in, we took a short walk to the Hoyt Arboretum to see the redwoods. Standing next to these giants made us feel tiny in the best way.

Close-up of blue spruce tree branches with dense, needle-like leaves; a taller evergreen tree and blue sky are visible in the background.
A large, historic mansion with red roof tiles, dormer windows, and ornate stonework, surrounded by trees and visitors in the foreground.
People sit and stand near a picnic table under a tree, overlooking a cityscape with buildings, hills, and a partly cloudy sky.
A scenic viewpoint with people sitting under large trees, overlooking a city and mountains in the distance; a chain-link fence runs along the edge of the overlook.
A person takes a photo of a scenic outdoor view with their smartphone, standing on a paved path surrounded by trees under a blue sky.
Three people stand close together and smile at the camera, with a cityscape and greenery visible in the background.
A man and woman stand smiling together in front of a fence with a view overlooking a cityscape, trees, and distant mountains.
Two people stand smiling in front of a chain-link fence, with a cityscape, trees, and mountains visible in the background on a sunny day.
Two people stand side by side in front of a fence with a cityscape and greenery in the background, under a partly cloudy sky.
View of a city skyline with tall buildings, surrounded by dense green trees and hills under a partly cloudy blue sky.
Map of the Hoyt Arboretum with color-coded walking trails, trail names, distance markers, and a legend indicating facilities such as restrooms, parking, and picnic areas.
A person stands on a wooden platform looking up at tall redwood trees in a dense forest under a partly cloudy sky.
A person stands with arms outstretched on a bench in a forest surrounded by tall redwood trees.
Two people stand with arms outstretched on a bench in a forest of tall redwood trees, with sunlight filtering through the branches above.
Tall redwood trees line a sunlit forest path with a wooden railing on the left and patches of blue sky visible through the tree canopy.
Two people stand on either side of a large tree trunk in a forest, smiling and waving at the camera. Ferns and greenery surround them.
Two people stand on either side of a large tree trunk in a forest, surrounded by green foliage and ferns, beneath a canopy of branches.
Two people stand with arms outstretched in front of a tall tree in a forest, smiling at the camera. Lush green foliage surrounds them.
Two people stand with arms outstretched and heads tilted back at the base of a large tree in a lush, green forest.

Sweet Detour: Pie Spot

Dinner plans were set for Luce, but with an hour’s wait, we wandered nearby and found Pie Spot. A flamingo mural caught our attention, and inside we discovered mini pies in irresistible flavors like banana cream salted caramel, lemon vanilla bean, and brown butter pecan. Naturally, we sampled all three.

Two people stand smiling in front of a mural featuring pink flamingos and a round sign that says "Pie Spot" on a turquoise brick wall.
People walk past a turquoise building with large windows and a round pink sign reading "pie spot" hanging above the entrance.
Three small pies on white plates sit on a speckled table in a cafe, with a counter and coffee machines visible in the background.

Dinner at Luce: Italian Comforts

Luce is small but mighty, and worth the wait. We shared mixed greens, nettle ravioli with butter and parmesan, rigatoni with fava greens and prosciutto, corzetti with walnut and ricotta pesto, garlic-oil cabbage, buttered turnips, and salt focaccia. Every bite was fresh and flavorful.

A white bowl of rigatoni pasta with greens and bacon, topped with grated cheese. A glass of water is in the background on a wooden table.
A close-up of a plate of mixed green salad with leafy greens and a light vinaigrette on a wooden table.
Two people wearing blue jackets smile at the camera while sitting in a cafe with shelves of bottles, jars, and plants in the background.
A close-up of stuffed ravioli in a light butter sauce, topped with grated cheese, served in a white bowl.
A light pink ranunculus flower in a glass bottle, next to a white cup, saucer, and sugar cubes on a wooden table.

Multnomah Falls at Sunset

We closed the day with one of Oregon’s most iconic sights, Multnomah Falls. We got there later in the evening, almost at sunset, and it ended up working in our favor. Since it was so late, we did not have to pay for parking and were able to snag a great spot right up front. Honestly, we were not even sure if the area would still be open because there were so few people around, but to our surprise, we were able to walk right up without any problem.

We started out on the lower landing of the falls, setting up to take photos and trying to decide if we had enough daylight left to make it up to the bridge. At first, we thought the walk was 2 miles, which made us hesitate. But we decided to start the hike anyway, and along the way we discovered it was actually only 0.2 miles. That made all the difference. Within just a few minutes we were standing on the bridge, mist from the waterfall brushing our faces, and it was absolutely worth it.

If you ever visit Multnomah Falls late in the day and are debating whether to go up to the bridge, do it. The short walk is quick and easy, and the photos from both the main landing and the bridge give you two incredible perspectives of this breathtaking landmark.

A car drives on a highway beside a large river, with mountains, trees, and a faint rainbow under a cloudy sky in the background.
A tall waterfall cascades down a rocky cliff surrounded by dense green trees, with a crosswalk and lamppost in the foreground under a partly cloudy sky.
A tall waterfall cascades down a rocky cliff surrounded by green vegetation and trees under a clear sky.
Tall waterfall cascades down a rocky cliff surrounded by greenery, with a black metal fence in the foreground and trees at the top of the cliff.
Silhouetted trees frame a sunset sky with scattered clouds tinted pink and purple, while the horizon glows with soft yellow and orange light.
A wooden bench sits on a paved path surrounded by dense green trees, with a colorful sunset visible through the foliage in the background.
A tall waterfall cascades down a rocky cliff surrounded by lush greenery, with a stone pathway and a person sitting near the base.
A tall waterfall cascades down a rocky cliff in two tiers, with a footbridge crossing between the upper and lower falls, surrounded by lush green trees.
A person holds a small camera facing a two-tiered waterfall surrounded by lush greenery, with a footbridge spanning the upper cascade.
A person stands at a railing, taking a photo of a tall two-tiered waterfall with a footbridge spanning the upper cascade, surrounded by lush green trees and moss.
A man in a blue jacket smiles at the camera while standing in front of a waterfall and a footbridge, surrounded by lush greenery at dusk.
A tall waterfall cascades down a rocky cliff surrounded by lush greenery, with a footbridge spanning between the upper and lower falls.
A tall waterfall cascades down a rocky cliff surrounded by trees, with a footbridge spanning the lower falls and people observing from below.
Three people smiling and posing for a photo in front of a waterfall with green mossy surroundings.
A tall waterfall cascades down a steep, rocky, green-covered cliff near a stone bridge, with a person standing and looking at the camera in the foreground.
A tall waterfall cascades down a rocky, moss-covered cliff surrounded by greenery, with a stone railing and pathway in the foreground.
A stone bridge crosses a forested ravine at dusk, surrounded by tall trees and dense greenery under a cloudy sky.
A man in a gray jacket stands smiling in front of Multnomah Falls with a stone bridge above the waterfall, surrounded by greenery.
Two people stand in front of a railing with a tall, two-tiered waterfall and an arched bridge surrounded by greenery in the background.
Two people stand with arms outstretched in front of a tall, cascading waterfall and a bridge, surrounded by lush greenery at dusk.
Three people smile for a selfie in front of a tall waterfall and footbridge surrounded by lush greenery at dusk.
A man stands next to a railing with a camera and tripod in front of a tall waterfall cascading down a rocky cliff, with a footbridge spanning the falls.
A man stands in front of a railing with a camera in hand, smiling, with Multnomah Falls and a bridge visible in the background.
A man stands with a tripod near a railing in front of Multnomah Falls, with a bridge spanning the waterfall in the background and dense greenery surrounding the scene.
A man smiles for a selfie in front of a tall, two-tiered waterfall and a bridge, holding a camera and smartphone, with greenery surrounding the scene.

Closing Thoughts

In one day, we experienced Portland’s food scene, creative spirit, and natural beauty, all while sharing it with family. We never felt rushed, yet we managed to see and taste so much.

If you are planning your own Portland adventure, take this as inspiration to create a day that is uniquely yours. Whether it is brunch at Elephant’s, a book hunt at Powell’s, or the rush of Multnomah Falls, Portland rewards curiosity at every turn.

Three people smiling in front of a metal fence with a waterfall and greenery in the background.

We want to hear from you:Did you end up going to one of these places? We would love to hear about your experience. DM us on Instagram @richandabigail

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