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    Home » Maine

    My Experience on a Walking Food Tour of Portland, Maine

    Updated: Jul 27, 2024 · Published: Jun 13, 2023 by Dave Lee

    The culinary scene in Portland, Maine, has much to offer travelers, and a walking food tour of the Old Port neighborhood is one of the best ways to begin. I recently had the opportunity to join an Old Port Culinary Walking Tour by Maine Day Ventures at no cost as part of my attendance at the AdventureELEVATE travel conference.

    Whether you're a seasoned foodie or simply curious about exploring Portland's culinary landscape, this walking food tour is a great way to discover the Old Port district. So, put on your walking shoes, bring your appetite, and prepare for a fun experience that will leave you with a newfound appreciation for the flavors of downtown Portland, Maine.

    An Andy’s Old Port Lager kicks off our 3-hour Portland food tour with Maine Day Ventures
    Andy's Old Port Lager

    First, I'd like you to feast your eyes on the Portland food tour as I experienced it. And then, I'll tell you more about the female founder, Pam, and her company.

    Table of Contents

    • Foodie Tour
      • 1. Andy's Old Port Pub
      • 2. Luke's Lobster
      • Portland Waterfront
      • Wharf Street
      • 3. Rigby Yard
      • 4. Dean's Sweets
    • Conclusion
    • About Maine Day Ventures

    Foodie Tour

    Artist, raconteur, and food guide. Timothy Goldkin is all three and more, as he demonstrated during a three-hour walking tour of Portland's historic Old Port. We met Tim at 1:30 p.m. on a Tuesday at the first stop on the tour.

    1. Andy's Old Port Pub

    Andy’s Old Port Pub
    The bar at Andy's

    At Andy's Old Port Pub, he led us from the front bar to the back room, where the walls were plastered with promotional posters for past performers. Everyone in our group took a seat, and Tim began telling us about the pub.

    On Commercial Street, which runs along Portland's waterfront area, Andy's Old Port Pub is a local favorite among fishermen, women, and nearby islanders. They often grab local craft beers before catching the last ferry home. The Casco Bay Lines ferry service is on a pier one block north of the bar.

    Andy's opened in 2007; however, the worn floorboards and exposed brick walls suggest that the building is much older. At this point, we were given a small glass of Andy's Old Port Lager by Island Dog Brewing, a brewery in South Portland, which I enjoyed.

    Fish taco at Andy's Old Port Pub, stop number one on our Portland, Maine food tour
    Fish taco

    Our first bite of food soon followed: a fresh fish taco made with haddock, cabbage, onion, pico de gallo, and lime crema. Andy's Old Port Pub's owners support sustainable fishing practices and source seafood from the Gulf of Maine. Their menu includes lobster bruschetta, fish and chips, lobster rolls and BLTs, shrimp po'boys, and pulled pork poutine.

    2. Luke's Lobster

    The second stop on our Maine food tour was Luke's Lobster Portland Pier
    Luke's Lobster Portland Pier

    Leaving Andy's, we strolled one block south on Commercial Street and hung a left onto the Portland Pier. At the far end was another of Portland's restaurants, and our next stop was Luke's Lobster. Here, Tim gave us the option to sit outside at picnic tables or inside. Despite the wind chill, we all chose the patio. The waterfront view alone was worth the visit. Tim was quick to inform us that we were on a working pier.

    To that point, Luke's is adjacent to the station where they buy their lobster. You won't find Maine lobster any fresher! Also, we could see a woman painting buoys for lobster traps on the pier. Rocky Bottom Fisheries provides lobster demo tours and sunset cruises in Casco Bay.

    Iced tea with lemon
    Iced tea
    New England clam chowder
    New England clam chowder

    Our drink at Luke's was a refreshing iced tea with lemon, and we had a hot cup of New England clam chowder with oyster crackers to eat. Tim also used this opportunity to tell us about Peaks Island, which he highly recommended we visit via the ferry.

    Portland Waterfront

    One of the reasons I liked Tim was that he was very passionate about Portland and the Old Port in particular. After leaving Luke's, we walked to the end of the Portland Pier and hung a right. The photo below shows what we were looking at when Tim talked about the slow gentrification of the Old Port neighborhood.

    Maine native Timothy Goldkin led our Portland food tour
    Our local guide, Timothy Goldkin

    The left shows old, somewhat rickety-looking buildings extending along Custom House Wharf. Contrast these with the newer buildings on the right, and you see where he was going. He also shared an enlightening anecdote about what it's like to empty an offshore lobster boat.

    Wharf Street

    Next, we crossed Commercial Street and walked another block to Wharf Street, a two-block cobblestone alley lined with historic buildings. Tim described it as Portland's version of Bourbon Street in New Orleans, at least on Friday and Saturday nights.

    Wharf Street in Portland's Old Port neighborhood
    Wharf Street

    But we were walking through this old cobblestone alleyway on a beautiful Tuesday afternoon, and you'd never know it's a raucous nightlife spot. Our guide stopped in front of a bar called Bar of Chocolate. He recommended it for the drinks and vibe. I'd come across it in my pre-trip research. Cocktails served with dessert sounds like a winning combination!

    3. Rigby Yard

    Entering Rigby Yard bar, our third stop on the food tour of Portland, Maine
    Entering Rigby Yard

    A few doors down was Rigby Yard, our third stop on Maine Day Adventures' Portland food tour. Here, housed in an industrial building formerly used to repair train cars, we sat at a large high-top table and were served a Lunch IPA Beer (7%) by Maine Brewing Co. in Freeport. I'd been wondering whether we'd be treated to a lobster roll on our walking tour, and the answer was yes!

    Related: Best Places To Eat in Bar Harbor

    Maine lobster roll with potato chips and a Lunch IPA Beer (7%) by Maine Brewing Co. at Rigby Yard
    Lobster Roll with a Lunch IPA Beer

    We received a 3-ounce cold Maine lobster roll with light house-made mayo and potato chips. Whole claw and knuckle meat were used, a sign you're getting the meatiest bits of the crustacean. This was my second lobster roll that day, as I'd gotten one earlier at the Bite of Maine food truck in Fort Williams Park. Of course, that didn't stop me from eating the entire thing and licking my fingers afterward.

    4. Dean's Sweets

    Chocolate truffles at Dean's Sweets, our last stop on a Portland food tour by Maine Day Ventures
    Chocolate truffles

    At this point, I was craving a sweet finish to our Portland food tour, and Tim delivered. Our fourth and final stop was Dean's Sweets, less than a block away on Fore Street. Co-owners Kristin and Dean Bingham began making chocolate from their home nearly 20 years ago and built a business from it before long. Over 30 varieties of hand-dipped chocolate truffles are made in the kitchen at their Old Port location.

    Every effort is made to source local food, such as:

    • Organic maple syrup tapped in Madison
    • Sea salt from Marshfield
    • Butter from Casco Bay Creamery in Scarborough

    If you have a nut allergy, you're in the right place. Their truffles don't contain nuts or nut products.

    Mint Julep chocolate truffle
    Mint Julep truffle

    Everyone on our Portland food tour by Maine Day Ventures got to try two chocolate truffles in the shop. The first was provided for us, and the second we could choose ourselves. I picked a delicious seasonal offering, Dean's Derby Mint Julep, made with spearmint and bourbon buttercream.

    Conclusion

    Over three hours of learning about the local history of this port city, we enjoyed the following:

    • Fish tacos
    • New England clam chowder
    • Lobster rolls
    • Handmade chocolates
    • Craft beers from Maine x2
    • Iced tea

    This is an example of the local cuisine your tour may include. However, some of the places you visit may differ. For example, maybe you'll end up at one of Portland's fantastic donut shops instead of a chocolate shop.

    An entertaining and knowledgeable guide makes all the difference between a fun walking tour and a boring one. Tim was an excellent tour guide, and while I know it's unrealistic for everyone who takes one of Maine Day Ventures' Portland food tours to get him, I'll keep my fingers crossed for you.

    The Old Port Culinary Walking Tour includes all food and beverages, plus the guide and gratuities for staff at the locations you visit. Tips for the guide are not included and are at your discretion.

    About Maine Day Ventures

    Pamela Laskey owns and directs Maine Day Ventures (formerly Maine Foodie Tours), which she began more than 12 years ago. According to her bio, building the tour business has been a "love-fest with the local Maine food scene, learning about dishes indigenous to this region and watching the creative culinary artistry grow in every direction." I had the chance to meet Pamela before my culinary tour began and later at the travel conference I was in Portland to attend. She's delightful.

    Maine Day Ventures currently operates culinary tours and historical walking tours in five cities:

    • Portland
    • Kennebunkport
    • Bar Harbor
    • Boothbay Harbor
    • Biddeford

    In Portland alone, there are tons more small-group food tours to consider. Hop on a boat for a Casco Bay Oyster Cruise, or take the Maine lobster roll-making class. There's even a "Doggy & Me" culinary journey to get your pup delicious food!

    _____

    My Portland food tour with Maine Day Ventures was provided at no cost in partnership with the Adventure Travel Trade Association and the Maine Office of Tourism as part of my attendance at AdventureELEVATE North America.

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    Dave Lee

    Dave Lee

    Food Writer

    I'm on a mission to find the best food in Texas and beyond.

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