Dugan is an expert tour guide and passionate about history! He provided a superb and detailed…read morehistory of African Americans in Portland, ME from the colonial era to the current day. We loved the amazing story of Susan Rice and her mother (Lois Rice) who each had a tremendous impact on education and public policy. Our family enjoyed learning about the many changes in downtown Portland from the 1700s to the 1950s and hearing the stories of remarkable leaders in the community over generations. We appreciated the enthusiasm and concern of Dugan to make sure the entire group was OK during the walk on a hot summer day (the shaded "rest breaks" were a plus). Also, he was open to questions and made everyone feel welcome. Overall, I would strongly recommend any of the walking tours! You are bound to discover something new.

What can I say, I had the pleasure of experiencing Dugan's walking tour today. You will be amazed…read moreby the deep understanding of the hidden history of this city. Dugan is very knowledgeable and has done extensive research of his topics. I was extremely pleased with his presentation and how he was able to weave in aspects of the rich but unfortunately not widely known historical facts by those outside of this city. As other reviewers have said the Susan Rice tie-in was something I did not expect. I would highly recommend this tour to anyone who wants to learn about this gem of a city. Dugan, thanks for your dedication and keep up the great Work. We all the better for it.

excellent experience! our guide, Gordon, is a terrific storyteller and our extended family group of…read moreadults laughed and learned local history in a fun setting. Highly recommend!

Gordon, our guide, was very engaging and entertaining! Our tour was about 1 hour and our group was…read morearound 10 people. I would recommend this tour for anyone looking to have a unique, off-the-beaten-path type of Portland experience.

This was a super interesting Locally owned tour of Portland . We visited some beautiful historic…read morelight houses and toured the downtown areas. The driver (and owner) had lots of local interesting information to share and he was enthusiastic and really made the tour fun for our group. Actually was one of the best local tours I have ever been on. Highly recommended when visiting Portland for the first time.

loved this tour! great commentary and good jokes! Very interesting and well done. I would…read moredefinitely recommend this trip!

We had a great time on this walking tour. Our guide Dugan brought Portland to life with interesting…read morefacts and stories. All questions were welcomed and answered. The tour starts on time, so don't be tardy to this highly recommended excellent tour.

Our group of five had a great tour with Pete on a crisp sunny day. Learned history and saw sites…read morefrom Monument Square to the waterfront area; the Eastern Prom, Portland Observatory and more. The guide was very knowledgeable and his sense of humor meshed well with our crew. It was pleasant 3+ mile walk that capitalized on some terrific views. The exercise helped whet our appetite for lunch at one of many restaurants Pete recommended.

My mum and I absolutely love red cloak tours!! The stories are very interesting and spooky. The…read moretour guide is really kind, and happily answers any questions. I went to the bath and wisscasset tours and found out so much about houses and places I may have overlooked if not for this new knowledge. Call me crazy, but I think I may have saw a ghost in the top window of a house in wisscasset, when nobody was home.

My family and I took this tour the other night. There were 12 people on the tour. Our guide…read morecombined stories about the history of the city as well as a number of different ghost stories. She was articulate and told some very good stories both as to the city and its origins and the different buildings that are haunted. At the end of the tour I kept looking in Opera House hoping to see the ghost that apparently still hangs out there. We all enjoyed the tour and would highly recommend it if you are visiting the town.

While visiting the Kennebunks, I decided to book my first ever foodie tour with Maine Day Ventures…read more This three hour tour not only covered delicious eats, but delivered in history. As our tour group visited each restaurant, we got a side of Kennebunkport history and the insider scoop as to where all of the locals dine. Marlene Brooks is an exceptional host and tour guide. She is a 13th generation Mainer and provided such detail about each local spot including the history behind our food. Her professionalism and Maine pride was evident throughout the tour. The ticket price for this experience was around $145. In my opinion, it is well worth the price because it is an opportunity to meet new people, learn more about Maine, and try different restaurants. Marlene took our group to some restaurants that my friend and I didn't know existed. Some advice would be to arrive on the tour hungry because you get to try so many delicious plates. By the end, my friend and I were full. Below please find some of the places we visited and the food we enjoyed: 1. Fiafia - mixed berry smoothie 2. Alisson's - lobster roll (you get a choice between three - the original, lemon garlic, or lobster chowder) 3. Federal Jack's - clam chowder with potatoes and a sample of beer 4. Mornings in Paris - whoopie pie and a choice of coffee or select tea 5. The Pilot House - fried haddock bites 6. Bar Harbor Cheesecake - cheesecake sample (can have more than one) This foodie tour encouraged me to try other food tours when traveling to new places. Marlene and Maine Day Ventures left a lasting impression and added great value to my Maine trip. The Kennebunks are filled with a rich history, excellent seafood, and the most friendly people. Thank you for a great experience!

A gourmet tour this is NOT. There is a world-class lobster roll place on the tour (Clam Shack), but…read morego there yourself and save yourself the rest of the garbage. Mead? Really? Undrinkable. Whoopie Pies? If you happen to like them, buy it yourself and the local grocery store. Our guide, a schoolteacher, treated us like idiots and managed to convey very little information. She couldn't even pronounce macaroon correctly, and she's leading a food tour? Do yourself a favor and skip this; go to one of the fantastic food tours in Portland ME instead.

I'm a little bit of a history geek, what can I say? I was the kid that relished the opportunity to…read moretalk to my grandparents about their lives growing up, what our community used to be like and look like, what their parents experienced. Finding old photos of towns and cities that I'm familiar with now are unbelievably fascinating, and preserving that which was is something near and dear to my heart. Which is why I'm a little in love with the The Greater Portland Landmarks, the safeguards of Portland's history via buildings, neighborhoods, and outdoor spaces. Through education and advocacy these great stewards of urban conservancy have helped to maintain some amazing spots throughout the city of Resurgam, while thoughtfully bridging the gap from the character of the city that was to the character that the city's beginning to have. I've had the opportunity to explore some of their catalog of public offerings, including Portland Observatory tours (https://www.yelp.com/biz/portland-observatory-portland), Custom House tours (https://www.yelp.com/biz/united-states-custom-house-portland), and a tour of the Homes of Portland's Golden Age (where we walked around the Spring Street Historic District [which was placed on the National Register of Historic Places in '71] and viewed an array of impressive architectural styles throughout the past couple centuries. That's just some of their ongoing events; they also host a lot of other awesome shindigs (like an annual decade-specific themed gala at a large mansion in Portland). The folks who work at GPL are dedicated, passionate, and well-versed in all things Portland. I care deeply about the past, present, and future of this great city, and I feel rest assured that there are others that do so as well!

Take their tours, donate, support this worthy and well-run cause…read more... In August, I was visiting Portland to eat and relax and look at the water. When my companion suggested (ah-hem, insisted) that we take the Greater Portland Landmarks walking architectural tour, I agreed but had no idea what I was getting into. Like, what? The headquarters or main building is on Spring Street behind the MFA, where I'd been several times already. It's a straight ten-minute walk from the Old Port area, so pretty easy to access. When we got there, we were greeted warmly by the staff and invited inside to wait for the tourists to gather. They allow (and encourage? insist upon?) on-line reservations, which we had. We pad electronically with credit cards using their portable chip reader. It was good to see historic preservation embracing technology. Ten bucks each, totally worth it. Our group of about ten tourists was led by two men, both school teachers, who tag-teamed the direction of the group and the speaking. They were warm and funny and kind and helpful and full of information. When one of them knew that the other was the expert, he'd say, And now XXXX is going to talk about the roofline of Federalist style buildings. Or some such. And the information is transferrable. I was recently in downtown Philadelphia where I was able to identify architectural styles that I learned about in Portland. The walk isn't that long distance-wise because they essentially keep close to the neighborhood around their building but it is strenuous and takes a while because they cover so much, including the Victoria House (from the outside). They encouraged questions and engagements and were helpful and attentive to those with limitations (slow walkers, the deaf, etc). At one point, we Zillowed the price of a house that was on the tour, which connected past and present. The guides even got us an inside tour of the private Cumberland Club. I would do it again. I would do their other tours (including of the Observatory on Munjoy Hill). If I lived in Portland....

I attended the Portland: Old Port Culinary Walking Tour on Sunday, June 14, 2026 at 10:30 am with…read moreAnne and Ross. Usually, there is only one tour guide and it was supposed to be Anne only but Ross joined in as well. The Old Port Culinary Walking Tour is a foodie tour with a mix of history and culture. Our group consisted of 13 people. The tour starts at Andy's Old Port Pub with an introduction from our tour guides. At Andy's Old Port Pub, we were seated in the backroom and had a seasoned, grilled fresh haddock with house-made pickled vegetables, pico de gallo and lime crema in a corn tortilla and Andy's house Lager. Ross talked about the suspicious happenings and history at Andy's Old Port Pub. They both talked about Harbor Fish Market which was right across the street and how the seafood never see the back of a truck. I thought the fish taco was okay and was probably my least favorite food item from the whole tour. Andy's house Lager was very smooth and I really enjoyed it. Then, we walked next door to Gilberts Chowder House where we had a choice of Clam Chowder, Haddock Chowder, Corn & Chicken Chowder, Seafood Chowder, or Seafood Chili. I chose the Clam Chowder. The Clam Chowder was thick and not as creamy as I usually like my clam chowders. Here, Anne was showing us pictures of lobster abnormalities. After having our chowder, we walked to the historic U.S. Custom House and old fishing docks. We even got a postcard of the old fishing docks which was a nice souvenir. Next, we stopped at Rigby Yard and were seated in a small private room. We were offered several drink options; I chose a glass of prosecco. We had the Fresh Maine Lobster Roll with fresh Maine lobster meat Maine-style, tossed lightly in mayo, lemon, and sea salt served on a brioche roll with chips. The lobster was definitely fresh and good. The last two stops were dessert spots: Dean's Sweets and The Gelato Fiasco. We had a needham which is a confectionery dessert bar made from sugar, chocolate, coconut, and potato and we had the option to choose another truffle. I chose a blueberry one. At The Gelato Fiasco, we were able to choose 2 different flavors. Funny enough, I had went to The Gelato Fiasco the night before and it really is delicious gelato. I was glad to try different flavors. The tour finished about 1:45pm. The tour guides thanked us for spending our time together. The Portland: Old Port Culinary Walking Tour was fun and I enjoyed meeting the other people in our group. Anne and Ross were very knowledgeable with Portland's history and food scene. They had good recommendations for other things to do in Portland. The food we had on the tour was okay according to my opinion, but it was definitely a good variety of Maine dishes.

We came to Maine very VERY early season (March 20th-24th) and were looking for something to do…read more Most of the area is still in full 'pre season' mode, with many restaurants and services closed, especially during the week. We found the walking Food tour on Viator and jumped at it - and boy were we glad that we did! Because of the time of year, my wife and I were alone on the tour and as such got to spend around 3 hours with our guide, Ray Sapirstein. Putting aside Ray's obvious love for Portland and food in general, he was a charming guy - keeping us engaged and entertained with stories about the area for the entire duration of the tour. Ray is a PHD trained historian and, as such, was able to fill in a lot of color about the area, going beyond the 'food' aspects of the tour, describing the 'hilly roads' which were sand dunes were covered up to build out the city. Add to that the fact that he took us to several places that we NEVER would have found via googling for 'best ofs' and would have been a HUGE failure to miss! Andy's Old Port Pub - a neighborhood bar (don't call it a dive, though in my mind it qualifies). Spend some time chatting with Thomas, the owner, and Steve the bartender - and had what I can only describe as the single best haddock taco I've ever had in my life. Do not judge a book by it's cover: this place is AWESOME. Great craft beer tap list, and a warm and friendly environment. If I lived in the area, this would be my regular. From there we went to Gilbert's Chowder house right next door - Ray was again right: don't sleep on the seafood chili - it was RIDICULOUSLY amazing. After that we paid a visit to the Harbor Fish Market where we got to see the recent catches, and as Ray pointed out the 'transparency' of the thing: fish are cleaned and prepped for sale right where the customer can watch, and all fish are labeled as 'fresh' (with VERY few pre-frozen exceptions). This is also the place to go if you want to buy Maine swag. From there we proceeded to Rigby House, an unassuming 'coffee shop and workspace' that Ray promised us had nothing short of the best lobster roll in Maine: I've had some good lobster rolls so I can't quite commit to that, but the bread it was built on was FANTASTIC, baked locally from one of the bakeries rated tops in the nation right in Portland. This stop came with either 2 samplers or 1 full pour from their 20+ menu. Don't miss the blueberry ale. It's a rare treat and again, came from Ray's love of his city. From there, we visited Dean's Sweet shop for a couple of truffles and terrible jokes, and then Fiasco's Gelato to round up our day - try the lobster gelato, it's weird and not something I'd necessarily do again...but glad to have had the experience. The whoopie pie gelato was top notch and the blueberry was one of the best gelatos I've ever had. For a 3 hour tour, with all food included, we were certainly full and happy. The walk was short - I don't think we wandered more than a mile in total - and when we were showing signs of being "Help me I'm not from Maine cold", Ray took us into Grittys, another neighborhood bar just for a warm up.