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Top Oregon Walking Tours

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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 …More

Portland, USA
4.3 (469)

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 (469)
from
$44
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 …More

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
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 …More

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
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 …More

Portland, USA
4.9 (628)

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 (628)
from
$69
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, …More

Likely to Sell Out
Likely to Sell Out
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 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 …More

Portland, USA
4.2 (51)

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 (51)
from
$29
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 …More

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

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 …More

Portland, USA
5.0 (234)

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 (234)
from
$107
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; …More

Likely to Sell Out
Likely to Sell Out
Portland, USA
4.6 (27)

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 (27)
from
$38
Streetcar Around Portland to Pearl, Slabtown, and Waterfront

Travel through four of Portland’s quadrants, and explore 8 to 10 of the city’s unique districts by foot and our European-style streetcar. Stroll, taste, see …More

Likely to Sell Out
Likely to Sell Out
Portland, USA
5.0 (16)

Streetcar Around Portland to Pearl, Slabtown, and Waterfront

Travel through four of Portland’s quadrants, and explore 8 to 10 of the city’s unique districts by foot and our European-style streetcar. Stroll, taste, see...

3 hours • Free Cancellation
5.0 (16)
from
$65
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 …More

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
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 …More

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

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 …More

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

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 …More

Likely to Sell Out
Likely to Sell Out
Portland, USA
4.8 (266)

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 (266)
from
$99
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 …More

Likely to Sell Out
Likely to Sell Out
Portland, USA
4.9 (184)

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 (184)
from
$189
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 …More

Likely to Sell Out
Likely to Sell Out
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 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. …More

Portland, USA
4.7 (150)

'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
4.7 (150)
from
$102
The Dark Below Portland Adults Only Haunted Ghost Tour

Beneath Portland's vibrant streets lies a darker story. Join The Dark Below and explore the city's most chilling legends, notorious crimes, and haunted landmarks. Journey …More

Portland, USA
5.0 (1)

The Dark Below Portland Adults Only Haunted Ghost Tour

Beneath Portland's vibrant streets lies a darker story. Join The Dark Below and explore the city's most chilling legends, notorious crimes, and haunted landmarks. Journey...

1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$35
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 …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
Downtown Portland Coffee and Donut Tour

Jumpstart your morning with a huge variety of coffee and donuts across 4-5 mouthwatering stops where each bite and sip was crafted right here in …More

Portland, USA
5.0 (38)

Downtown Portland Coffee and Donut Tour

Jumpstart your morning with a huge variety of coffee and donuts across 4-5 mouthwatering stops where each bite and sip was crafted right here in...

2 hours 30 minutes • Free Cancellation
5.0 (38)
from
$69

Frequently Asked Questions

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

Recent tour reviews
Do this donut tour
New York City
Portland’s Original Delicious Donut Adventure & Walking Food Tour
X2235OFbrianh, Sep 2026
Do this donut tour
Sebastian was really interesting and friendly and it was a great tour. Would defo recommend
Read more
Awesome Portland Food Tour
New York City
Portland Downtown Food Tour: 6 Tastings of Local & Global Flavors
wilsonvillemike1, Sep 2026
Awesome Portland Food Tour
Rebecca, did a great job. I have lived in the Portland area for over 25 years and I learned so much more during this tour. I would recommend doing this food tour, great food and great info on Portland.
Read more
Great overview of Portland
New York City
‘The Best of Portland’ City Tour: Small-Group Sightseeing Tour
katiebW9586VI, Sep 2026
Great overview of Portland
Great job by our guide - nice voice & lots of interesting information. Comfortable van & enjoyed the stops.
Read more
Rebecca rocks!
New York City
Portland Downtown Food Tour: 6 Tastings of Local & Global Flavors
Marilyn_S, Sep 2026
Rebecca rocks!
Rebecca was wonderful! We had a great tour today. We had a couple glitches when a planned stop closed unexpectedly, but that was in no way Rebecca’s fault. She had spoken to the establishment the day before and all was good, so something unexpected happened. My whole point in mentioning this, is to say it did t ruffle her feathers or throw her into a panic. We ended up at Jake’s and had amazing etouffee. Lots of great food and we learned things we did t know about Portland which was so much fun.
Read more
Streetcars Named VERY Desirable!
New York City
Streetcar Around Portland to Pearl, Slabtown, and Waterfront
Josdaughter, Sep 2026
Streetcars Named VERY Desirable!
Look no further for the best street car/walking tour of Portland. Kelly and Nancy were phenomenal tour guides. I will be back and will bring friends and family. Portland is a beautiful, interesting, historic city and viewing it in this way with these guides was spectacular!
Read more
Very pleasant and easy tour!
New York City
Portland’s Original Delicious Donut Adventure & Walking Food Tour
sarafE2314CB, Sep 2026
Very pleasant and easy tour!
Very awesome tour with Eric, who was very knowledgeable about both Portland and the donut scene. Highly recommend as two new locals who just moved to the city and wanted to learn a bit more about the city and local food spots!
Read more
Very knowledgeable about the whole history of the town and food!!!
New York City
All-Inclusive Downtown Portland Food Tour
Lori_C, Sep 2026
Very knowledgeable about the whole history of the town and food!!!
Dress for the weather, a jacket if needed. Also a good amount of walking, just like the description says.
Read more
Wine and waterfalls
New York City
Columbia Gorge Waterfalls & Wineries from Portland: All-Inclusive Afternoon Tour
M7173VRangelf, Sep 2026
Wine and waterfalls
If you are looking for the Easy Button to an amazing experience combining nature and a stop for local wine, this is it. Our guide, Luke, elevated the trip a notch beyond with his delightful manner and extensive knowledge.
Read more
David provided an...
New York City
All-Inclusive Downtown Portland Food Tour
Joann_O, Sep 2026
David provided an...
David provided an excellent tour. Variety of food. He was humorous, knowledgeable and engaging. The tour lasted approximately 4 hours. We saw and learned a lot about the area.
Read more
Fabulous underground tour
New York City
Shanghai Tunnels Underground Tour – with Beer Tasting
Keeleyrobbo, Sep 2026
Fabulous underground tour
This tour is so much fun (whether you believe in ghosts or not!). Skippy our tour guide was brilliant and very immersed in the story of Nina! We didn’t stay for pizza, but it t smelt amazing!
Read more
Great first day intro to Portland
New York City
‘The Best of Portland’ City Tour: Small-Group Sightseeing Tour
Cassmixer, Sep 2026
Great first day intro to Portland
Luke was absolutely great! I did the half day on my first day in Portland. It gave me the perfect cursory lay of the land to better plan the rest of my vacation. Luke was a fountain of knowledge on the local history and culture. Also, a great source for further recommendations. He made sure everyone was engaged and getting what they wanted from the tour. Would definitely recommend.
Read more
Luke was an excellent...
New York City
Columbia Gorge Waterfalls & Wineries from Portland: All-Inclusive Afternoon Tour
Kristi_B, Sep 2026
Luke was an excellent...
Luke was an excellent guide! We had the best time! He was knowledgeable about the area and very upbeat!
Read more
All you need to get acquainted with Portland!
New York City
Streetcar Around Portland to Pearl, Slabtown, and Waterfront
Deborah_C, Sep 2026
All you need to get acquainted with Portland!
What a fabulous morning spent with Kelly traversing the neighborhoods by streetcar and walks! You will see the most important sites, learn their history and most importantly, do walks through the most beautiful and historic neighborhoods in town. Kelly is a totally delightful and cheerful guide who will make your Portland visit most memorable!
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
The best food and city tour!
New York City
Downtown Portland Coffee and Donut Tour
stephaniepQ5521ZP, Sep 2026
The best food and city tour!
Evangel was so knowledgeable and fun! We learned so much about the city, coffee, and donuts! Highly recommend this 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
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