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Top Oregon Walking Tours

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Oregon Tours

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Shanghai Tunnels Underground Tour - with Beer Tasting
Portland, USA
4.3 (468)

Shanghai Tunnels Underground Tour - with Beer Tasting

This tour is the only access to Portland's underground Shanghai Tunnels with a new bonus visit to the 2nd floor and ballroom of the haunted...

1 hour 30 minutes • Free Cancellation
4.3 (468)
from
$44
Phantoms, Penance, and Poltergeists: Portland Ghost Tour
Portland, USA
4.4 (362)

Phantoms, Penance, and Poltergeists: Portland Ghost Tour

Embark on a spine-chilling journey through Portland’s eerie streets with our engaging walking ghost tour! Guided by a seasoned local expert in haunted history, this...

1 hour • Free Cancellation
4.4 (362)
from
$26
Intro to Portland Small Group Walking Tour
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.8 (324)

Intro to Portland Small Group Walking Tour

10 a.m., 1:30 p.m., 4 p.m. Start at DIRECTOR PARK Our downtown Portland, Oregon walking tours are engaging, well-paced and colorful: the Best of the...

120 to 150 minutes • Free Cancellation
4.8 (324)
from
$29
Portland's Original Delicious Donut Adventure & Walking Food Tour
Portland, USA
4.9 (622)

Portland's Original Delicious Donut Adventure & Walking Food Tour

We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't...

2 hours • Free Cancellation
4.9 (622)
from
$69
Portland Ghosts Boos and Booze Haunted Pub Crawl
Portland, USA
4.2 (50)

Portland Ghosts Boos and Booze Haunted Pub Crawl

Come on our chilling Haunted Pub Crawl tour presented by US Ghost Adventures! On select nights, explore the haunted streets of Portland, sip on local...

2 hours • Free Cancellation
4.2 (50)
from
$29
Haunted Pub Tour
Portland, USA
4.6 (174)

Haunted Pub Tour

Portland's longest running Ghost Tour with 300+ 5 star reviews. The city's wicked and wild history will blow you away! On this spine-tingling walking tour,...

2 hours 30 minutes • Free Cancellation
4.6 (174)
from
$45
Portland Pizza Walking Tour: 4 Stops, Full Slice Each
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.9 (67)

Portland Pizza Walking Tour: 4 Stops, Full Slice Each

Portland takes pizza seriously—and this tour is the easiest, most fun way to taste the scene in one walk. You’ll hit four pizzerias on a...

2 hours • Free Cancellation
4.9 (67)
from
$75
All-Inclusive Downtown Portland Food Tour
Portland, USA
5.0 (231)

All-Inclusive Downtown Portland Food Tour

Explore the essential food and drinks at the heart of downtown Portland, Oregon on this all-inclusive walking tour led by an experienced, professional, Portland-native guide...

3 to 4 hours • Free Cancellation
5.0 (231)
from
$107
Northern Oregon Coast Day Trip to Cannon Beach Area
Portland, USA
4.9 (57)

Northern Oregon Coast Day Trip to Cannon Beach Area

This day trip is a tour along a section of rugged coastline along Oregon's northern coast. The trip will include a history stop, a short...

8 to 9 hours • Hotel pickup offered • Free Cancellation
4.9 (57)
from
$139
Weird Portland Pub Tour
Portland, USA
4.6 (26)

Weird Portland Pub Tour

This tour is a must-do for anyone who likes beer and is interested in Portland’s artistic flair. Skip those boring tours about the Founding Fathers;...

3 hours • Free Cancellation
4.6 (26)
from
$38
Portland's Best Chocolate and Coffee Walking Tour
Portland, USA
4.9 (31)

Portland's Best Chocolate and Coffee Walking Tour

Portland's chocolate scene is overwhelming; let us navigate you through its origins, passionate makers, and diversity with this walking tour that delves into what some...

2 hours 30 minutes • Free Cancellation
4.9 (31)
from
$69
Portland Ultimate Dead of Night Tour
Portland, USA
4.6 (39)

Portland Ultimate Dead of Night Tour

Explore Portland’s dark side on this thrilling outdoor walking ghost tour through the city’s most haunted historic sites. Led by expert local guides, you’ll uncover...

1 hour 30 minutes • Free Cancellation
4.6 (39)
from
$27
Portland Downtown Food Tour: 6 Tastings of Local & Global Flavors
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.8 (261)

Portland Downtown Food Tour: 6 Tastings of Local & Global Flavors

Join Secret Food Tours through Downtown Portland, Oregon. Delight in the fusion of international flavors with locally sourced and crafted ingredients, showcasing the vibrant diversity...

3 hours 30 minutes • Free Cancellation
4.8 (261)
from
$99
Columbia Gorge Waterfalls & Wineries from Portland: All-Inclusive Afternoon Tour
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.9 (182)

Columbia Gorge Waterfalls & Wineries from Portland: All-Inclusive Afternoon Tour

Experience two of the greatest attractions of the Pacific Northwest – the Columbia Gorge Waterfalls and Oregon wines! Hear amazing narratives that lie beneath the...

6 hours • Hotel pickup offered • Free Cancellation
4.9 (182)
from
$189
'The Best of Portland' City Tour: Small-Group Sightseeing Tour
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.6 (149)

'The Best of Portland' City Tour: Small-Group Sightseeing Tour

Experience the Pacific Northwest’s most-dynamic cultural hub on this small-group tour of Portland's highlights! Explore diverse neighborhoods with your Cool Destinations 'Hall of Fame' guide....

4 hours • Hotel pickup offered • Free Cancellation
4.6 (149)
from
$102
Forest Park Urban Hiking Tour, Portland
Portland, USA
4.8 (85)

Forest Park Urban Hiking Tour, Portland

When tour guests asks us, "what one thing should I not miss in Portland," we pick the 5-mile (8-10 km) hike in Forest Park. No...

3 to 4 hours • Free Cancellation
4.8 (85)
from
$59
The Vibrant Kerns Hood - East Burnside and more
Portland, USA
4.9 (71)

The Vibrant Kerns Hood - East Burnside and more

In this Portland food tour, we will explore the charming streets of the Kerns neighborhood where we will sample some of the tastiest bites that...

3 hours • Free Cancellation
4.9 (71)
from
$119
Explore Columbia River Gorge Half-Day Small-Group Tour
Portland, USA
5.0 (39)

Explore Columbia River Gorge Half-Day Small-Group Tour

The 85-mile (137-km) long Columbia Gorge NSA would be a national park if it weren't a critical transportation corridor. It features waterfalls, mountains, monoliths, terraces,...

3 to 4 hours • Free Cancellation
5.0 (39)
from
$89
The Bustling Buckman Hood - Hawthorne, the Goat Blocks and more
Portland, USA
4.9 (37)

The Bustling Buckman Hood - Hawthorne, the Goat Blocks and more

Come on and let’s explore the bustling streets of the Buckman neighborhood. All the while this Portland culinary tour will take us to some of...

3 hours • Free Cancellation
4.9 (37)
from
$119
Brunch on Mississippi Food Tour
Portland, USA
5.0 (21)

Brunch on Mississippi Food Tour

Let’s have fun strolling the delightful and historic Mississippi district, while eating brunch! This neighborhood is a perfect way to experience a food tour in...

3 hours • Free Cancellation
5.0 (21)
from
$119

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
It’s walking through many...
New York City
Portland Downtown Food Tour: 6 Tastings of Local & Global Flavors
ELIER_D, Sep 2026
It’s walking through many...
It’s walking through many blocks of downtown with all of its good and ugly sides. Just don’t let that hold you back from taking this great tour.
Read more
5 Stars for Natasha! Incredible History, Spooky Tunnels & Great Beer!
New York City
Shanghai Tunnels Underground Tour – with Beer Tasting
Gersongarcia67, Sep 2026
5 Stars for Natasha! Incredible History, Spooky Tunnels & Great Beer!
This 90-minute tour is an amazing mix of dark history and spooky fun. Natasha, our guide, was absolute perfection. She was funny, incredibly smart, and her storytelling kept everyone completely captivated the entire time. She really brought the history to life! Walking down into the dimly lit, dusty brick tunnels feels like stepping back in time. You have to duck under low pipes and watch your step on the uneven floors, which adds to the raw, authentic adventure. Natasha shared chilling stories about the old days and even introduced us to the history of the resident ghost, Nina. We also visited the haunted second-floor ballroom in the historic Merchant Hotel.
Read more
A Fun Experience!
New York City
Shanghai Tunnels Underground Tour – with Beer Tasting
Paul_S, Sep 2026
A Fun Experience!
Not for the faint of heart. Very dark. Bumped my head several times. But interesting history, architecture, and ghost stories. Doug was a fun, knowledgeable guide.
Read more
David our guide was super...
New York City
All-Inclusive Downtown Portland Food Tour
Darry_J, Sep 2026
David our guide was super...
David our guide was super knowledgeable not only about Portland’s food cart culture but also Portland’s unique history. Not to be missed and come hungry.
Read more
Donuts plus city tour
New York City
Portland’s Original Delicious Donut Adventure & Walking Food Tour
talltraveler53, Sep 2026
Donuts plus city tour
Guide Erik was fantastic, knowledgeable, friendly and flexible. Lots of donut, history and cultural info
Read more
Fun Food Tour
New York City
All-Inclusive Downtown Portland Food Tour
KDDATL, Sep 2026
Fun Food Tour
Great tour & value !!! David our guide was knowledgeable and entertaining. He had a passion for the city, culture, and a foodie. You get more then just small bites expect to get good portions and array of flavors. Perfect amount of stops, city stories, and distance covered. Easy and fun walking tour.
Read more
Perfect first day in Portland
New York City
Portland’s Best Chocolate and Coffee Walking Tour
F3049VGnickr, Sep 2026
Perfect first day in Portland
We did the tour on the first day of our trip in Portland and it was the perfect introduction to the city. Our tour guide, Nanci, was incredibly friendly, cheerful, and she had tons of knowledge to share about the local businesses that we visited on the tour. We got to hear fascinating stories about the chocolatiers and coffee roasters as we tasted the amazing coffee and chocolate from each stop. Nanci was also happy to share the history of the different buildings and neighborhoods that we walked through, which really made the tour special! The coffee and the chocolates were delicious and we ended up revisiting a few of the stops at the end of the trip! I would absolutely recommend this tour and specifically, Nanci, to anyone looking for an introduction to Portland!
Read more
Have a leisurely morning and a full Oregonian afternoon (complete with wine!)
New York City
Columbia Gorge Waterfalls & Wineries from Portland: All-Inclusive Afternoon Tour
emilyrB4361KS, Sep 2026
Have a leisurely morning and a full Oregonian afternoon (complete with wine!)
If you want to see Portland's local mountains (volcanoes!), be surrounded by towering trees and iconic waterfalls, catch the little details of plants, osprey, king salmon, and banana slugs, and enjoy a picturesque, relaxing wine tasting with small-bite pairings at a local Oregon winery - without having to figure out the mountains, logistics, timing, fees, directions, or who's going to be the designated driver - this is the perfect tour for you!We had a long weekend in Portland - went to o concert Saturday night, enjoyed a late-morning brunch Sunday, and then rolled out of our hotel at 1 PM for our tour. We were greeted by Luke, who turned out to be a ridiculously good tour guide - passionate, incredibly knowledgeable, and someone who genuinely lives the spirit of the PNW. Not only does Luke know an incredible amount about the history of the area, but he's also knowledgeable about current issues impacting this magical region. He was a true professional when it came to safety, awareness, and making sure everyone had the best possible experience.We also lucked out with our group - eight interesting people from different parts of the country. There were plenty of laughs throughout the day, which made an already great experience even more fun. And the smaller group meant we could actually hear Luke, weren't constantly waiting on a huge group, and had plenty of time at each stop without feeling rushed.We will definitely be booking more adventures through Evergreen Escapes on future travels.Because as Luke showed us - "the Pacific Northwest WANTS you to live!"
Read more
10/10, Do Recommend!
New York City
Portland Downtown Food Tour: 6 Tastings of Local & Global Flavors
rebeccajJ9432SQ, Sep 2026
10/10, Do Recommend!
Rebecca was an amazing tour guide! She did a great job speaking to the history of the Portland, its architecture, and its food. She was also very engaging and made great food selections. Definitely recommend!
Read more
Scary yet funny
New York City
Phantoms, Penance, and Poltergeists: Portland Ghost Tour
chetana_c, Sep 2026
Scary yet funny
It was really great experience, Brendon narrated stories very interesting and humorous way. Enjoyed thoroughly.
Read more
Fun way to see another side of Portland!
New York City
Phantoms, Penance, and Poltergeists: Portland Ghost Tour
JandL_travelers, Sep 2026
Fun way to see another side of Portland!
The ghost tour through Portland was awesome! Our tour guide was super knowledgeable and took us to all the spooky locations and even had EMF meter! It was a cool way to see the city on our first night there and get a little taste of the unique history that some people may not have heard. Would definitely recommend! Great tour!!
Read more
Marcus
New York City
Explore Columbia River Gorge Half-Day Small-Group Tour
Michael_W, Sep 2026
Marcus
Marcus was an excellent guide. His knowledge of flora and fauna added much to the tour. He’s was kind and pleasant.
Read more
Great donut tour with city sites thrown in too.
New York City
Portland’s Original Delicious Donut Adventure & Walking Food Tour
mollymU6910VM, Sep 2026
Great donut tour with city sites thrown in too.
We had a very pleasant walk around town and sampled donuts from several places. The guide told us about some key sights in the downtown area in between stops. He was able to answer a variety of questions about the area and make recommendations for other restaurants besides just donut stores.
Read more
Great way to sample multiple pizza joints.
New York City
Portland Pizza Walking Tour: 4 Stops, Full Slice Each
mollymU6910VM, Sep 2026
Great way to sample multiple pizza joints.
A great opportunity to try out several pizza places. Each one was a little different in terms of taste and offerings. At each place we were able to select the type of pizza that we preferred.
Read more
Worth it
New York City
The Bustling Buckman Hood – Hawthorne, the Goat Blocks and more
Getaway17103055416, Sep 2026
Worth it
well I went here as it was recommended by a friend and she had said that I NEEEED to try this, and honestly she was right. But I can't tell you why because I am part of the secrete service and was actually taking care of a case. but I rate 5 stars!
Read more
Excellent guide!
New York City
Intro to Portland Small Group Walking Tour
Q5168LMkatherinem, Sep 2026
Excellent guide!
Excellent experience. Our guide was knowledgeable and extremely welcoming.
Read more
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