A Walk Through Time Tour In Portland

The best part was how Ross connected all these places into one big story. We weren’t just looking at old buildings; we were learning how fires, immigration, commerce, politics, food, and people shaped the Portland we see today. We walked away with a whole new appreciation for this city—and a camera full of pictures to remember it all! Ross even treated us to cookies at a special bakery before we finished. What a day! Ross was an exceptional guide who went above and beyond to make this tour memorable. His knowledge, storytelling, and ability to connect Portland’s history to the places we visited made this so much more than an ordinary walking tour. We highly recommend this experience to anyone visiting Portland!

A great tour! Marcia, our tour guide, was excellent! She was very knowledgeable and funny! I felt she added a personal touch to many spots we saw and discussed! While she is no spring chicken, we all had to hoof it to keep up with her!

I really enjoyed this tour. Ross was our guide and his knowledge was excellent and his humor made the tour fun. Definitely recommend this tour.

Ross was an excellent guide and was very aware of how his clients were handling the walk. His historical knowledge of Portland was exceptional and his humor was a bonus. I would definitely recommend this tour.

We were unable to go on this excursion. I tried to cancel with Maine Day Ventures but was told I had to call Viator. I couldn't find a number so had to pay anyway. Disappointed in the service.

Ray was excellent guide. Very knowledgeable esp about food and American history. Ask for Ray when you sign up.

Ross was a wonderful guide. He was happy to answer questions and co more in-depth about things we were especially interested in.

What an interesting and informative walk through time! Our guide, Ross, was great explaining the history of the area and answered any questions we might have. I would definitely recommend this experience to anyone visiting Portland!

Ross was a passionate and enthusiastic tour guide for Portland. He knows all the history and secrets of the town. It is well worth the time to spend a few hours with him. We would highly recommend this tour.

Interesting tour with a witty and knowledgeable guide who went out of his way to show us memorable places.

Ross was an excellent guide! He made all the difference.

Ross, our guide, was very knowledgeable and entertaining on our walk around Portland. Highly recommend!

wonderful private tour for two couples. remarkable tour guide with so much to offer in such an interesting and exciting manner. Ross was fantastic. could not have been a better experience

Really enjoyed the Maine History Tour. John was the tour guide. He was excellent. He was very knowledgeable and entertaining. We learned a lot. Definitely worthwhile.

Yanni I our tour guide was full of interesting information. You could tell he was proud of his cities history and present day culture. My husband and I enjoyed the experience very much.

Very interesting tour with lots of walking. Our guide gave us a lot of information, fun stories , and took us to much more than typical tourist spots. By the end of the tour we had quite a few recommendations for restaurants and things to do, which really made our trip.

The guide, Ross, was wonderful. He knew the history, the architecture, and so many of the people we passed. He had a great sense of humor, and spent as much time with us as we wanted.

Yanni was a wonderful tour guide. A Portland native, very young but very knowledgeable! Made the tour very enjoyable and made me appreciate and like Portland even more!

Excellent, friendly guide thru Portland history! Very interesting historical facts and sites in relaxing pace.

We thoroughly enjoyed our guide Yanni, he was very knowledgable about the history of Portland. He was patient and answered everyone’s questions thoughtfully. The walk was totally manageable and our weather was beautiful. The cookie at the end was a wonderful treat.

We really enjoy a good walking tour when we are visiting a new place to learn about the history. Our guide, Tyler, was as good as it gets. He was so knowledgeable and personable. He kept us engaged and taught us so much about Portland.

Ty was an amazing tour guide! He gave us entertaining stories about Portland history and the various buildings. We wish him the best on his new adventures in Duluth.

The tour was fantastic! Ross was the Best Guide Ever! He's fun, passionate about history and gave us great understanding of the history, culture, quirkiness, art, ghosts, food and sights that are Portland. He took us on a few "behind the scenes" access to historical buildings with interesting history, and pointed out the best views, restaurants and other sights to see based on our interests. He even sang a fun little song for us! (and did a great job) I can't recommend the tour- or Ross, highly enough. We left loving Portland and look forward to going back.

Great walking tour! We learned so much from Ty and Portland’s history was riveting. Highly recommend!

Did the walking tour with John today. Very informative. Walked all around the old port area and harbor. Went into the custom house. This is a cool way to see the city and come away with a lot of info.

Walk through Old Portland. Focus was on the history of the town and the architecture. Great guide. Our sneak peak into the Customs Building was a perfect ending.

Excellent historical tour of Portland! Tyler did a great job and even gave us chocolate chip cookies from a local bakery at the end of the tour. The tour was well paced and very informative. Tyler also showed us books on the history of Portland if we wanted to read more on the topic. Highly recommend this tour! Thanks Tyler!

Tour Guide was outstanding. Started on time, excellent historical knowledge, and spoke up so everyone could hear. Great!

It was a great very informative tour. It was just me, my wife , and our guide Tyler who did a great job and knew a lot about Portland. As someone who loves history, I feel like I learned a lot! There some really interesting Revolutionary War trivia to learn as well. Highly recommended.

Our guide was right on time and we finished on time. He was very respectful of people in the group schedules. He was very-very knowledgeable. I especially enjoyed the parts that explained the evolution of the different architecture styles. And the connection of some of the buildings use for the Underground Railroad.

Very knowledgeable local guide that really loves his subject. Extremely interesting and historical narrative. Excellent tour.

My husband and I had a terrific tour with our flexible, knowledgable, and personable tour guide, Ty. He was well-informed, able to answer all our questions, and had a range of knowledge, including political history, social history, architectural history, etc. I feel like I could take this tour again and again, and learn new things every time. And we simply enjoyed Ty's company, on top of all the interesting info. It was worth every penny to us.

Great time! We learned a lot about local history

Portland history tour in the winter! Ross was fantastic and made learning about this great city memorable. Best walking tour, even with frigid temps!

This was an excellent tour. The guide was enthusiastic and knowledgeable, offering an engaging account of Portland’s history and the experiences of early settlers through the 1900s.

We did a walking tour through old Portland. Even though it was frigid outside, we bundled up and our guide kept us so fascinated with historical facts we didn’t even notice! Tyler was an excellent guide and is very passionate about the history of this City. His passion was infectious. And, at the end of the tour, he presented us with delicious chocolate chip cookies from a local bakery!

I’ve been on many such tours and this one stood out because of the quality of our guide. First, he knew the history of the area inside and out (and recommended specific books throughout the tour if you wanted to know more). Second, he delivered his knowledge in a clear, well-paced manner such that even those in the back of the group could hear him well; he never sounded rehearsed. Third, he had a dry sense of humor and was approachable with questions. All four of us in our group, some of whom have lived in Portland for years, enjoyed our tour. Well worth the price.

The tour was very informative and our guide was extremely knowledgeable of Portland history and architecture! I highly recommend this walking tour!

Our guide Ross was excellent, very knowledgeable and made the cold temperature bearable. We had no idea Portland was as safe as a kitten.

This was an amazing experience our guide Tyler was so well read and obviously has a deep passion for history. He was a story teller who studies his craft through podcasts and avid reading so he can share unique historical facts about Portland. He has an amazing ability to draw you in to his narrative so you feel like you have been taken back in time! I would highly recommend this tour!

Tyler was an incredibly knowledgeable and personable guide! We will definitely recommend this tour to friends -- great for anyone interested in history and/or architecture and who would enjoy walking the streets of Portland!

Absolutely do not miss this tour! A wonderful walk around Portland with lots of history included! So much to see! The buildings will leave you speechless!

Ross was an awesome guide!!! Very knowledgeable and fun, he made sure to answer all of my son’s questions

My wife and I took the Walk Through Time tour with Tyler and really enjoyed it. Tyler was knowledgeable and enthusiastic about Portland’s history. He shared interesting stories about the city’s maritime past and pointed out architectural details we wouldn’t have noticed on our own. Tyler was engaging and answered all our questions. He made the tour informative without being dry. We’d definitely recommend this tour if you want to learn more about Portland’s history. Thanks, Tyler!

We had an amazing walking tour. Just enough information to digest. 100% recommend. The light rain made it even better.

Great way to see the city, learn the Historical relevance, and get your bearings! Would highly reccomend. Ross was great, a wealth of information and very entertaining!

We loved the tour, so full of fascinating information that brought the city alive for us. Great stories about the people and the places

Ross is truly the best tour guide in Portland. A great blend of history, some architecture and fantastic sights. He knows his stuff! Don't hesitate, book it!

Anne, the tour guide, was excellent! She used to be a teacher and was so thorough in explaining all the cool stories about Portland. It was a nice easy walk thru town and Anne pointed out all the great architecture as well. The waterfront area is very picturesque and there are lots of shops nearby. We were on a cruise ship and the start and end point for the tour was only a 5 minute walk away from the pier. Very convenient! And at the end of the tour we got a delicious chocolate chip cookie! I’d highly recommend this tour!