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Maine Walking tours

Our most recommended Maine Walking tours

Portland: Old Port Culinary Walking Tour

1. Portland: Old Port Culinary Walking Tour

Enjoy this experience that showcases the culinary culture of Portland, Maine comprised of talented food and beverage artisans, from bakers and brewers to confectioners, chefs, and more. Visit the spots the locals enjoy visiting on a daily basis. Join a friendly and engaging tour guide as they take you to several Old Port and neighboring artisanal shops, restaurants, and pubs. You’ll sample a delectable mix of classic Maine, Maine-inspired, up-and-coming, cultural, fancy foods, and beverages.  Meet and greet culinary artisans along the way, learn what inspires them and how they got their start with a lively narration from your guide. Along the way, your guide will dish about the colorful, social, and culinary history unique to the “Port City” with lots of additional recommendations on how to dine and imbibe. You are sure to leave full of delicious food and local history. This experience works with gluten (not celiac), seafood, nut, and vegetarian dietary preferences and sensitivities to the best of our ability. Guests may pick and choose their participation for any further food issues. Your foodie experience may include: fresh-picked lobster, from-scratch confections, locally-sourced temaki (raw fish) roll, Maine seafood “chowdah”, iconic Maine craft beer, Maine honey wine, and dark chocolate truffles made with Aroostook County potatoes.

Portland, Maine: 2-Hour Guided History Tour

2. Portland, Maine: 2-Hour Guided History Tour

Meet your local guide, a history lover who will bring the stories and facts from Portland’s past alive throughout the tour. Starting on Commercial Street, walk through the cobble stone streets of the historic Old Port, downtown, and waterfront areas.  Some of the locations that may be featured as part of the tour include the lobster statue, the home of Henry Wadsworth-Longfellow, the Eastern cemetery, the Abyssinian Church, and more. Your tour will finish on a sweet note with a local treat.

Portland, Maine: Hidden Histories Downtown Walking Tour

3. Portland, Maine: Hidden Histories Downtown Walking Tour

Discover Portland's hidden histories on a guided walking tour of the Old Port, downtown, and the working waterfront. Marvel at images of the past and at the colorful storytelling your guide shares with you to make the past come alive. Hear stories only a local knows about the city's sights, streets, and buildings. Explore the Old Port, Portland's major public buildings, and the working waterfront, winding through intimate cobblestone streets along the way. See the city's charming red-brick buildings, its waterfront filled with seafood restaurants and sea views, and more. Learn fascinating anecdotes and facts about Portland, sharing them with friends down the line to show your newly-gained local knowledge. End your tour in a waterfront park, about a 5-minute walk from where you started, surrounded by boutiques, restaurants, and other activity opportunities to continue your own discovery of the city.

Portland, Maine: Old Port Brewery Walking Tour

4. Portland, Maine: Old Port Brewery Walking Tour

Spend the day walking, talking, and tasting your way through the historic city of Portland, Maine. Led by a local guide, this 3-hour walking tour takes you through the interesting history of the city's beer culture. From becoming the birthplace of Prohibition in 1851 to establishing the first craft brewery in all of New England in 1983, Portland has a riveting story to tell.  Walk, Talk, & Taste (3 hours) Walk and talk with a local beer history guide through Portland's Old Port with tasting stops at Shipyard Brewing Company, Gritty McDuff’s, and Liquid Riot Bottling Company All tours end with drop-off at Old Port Spirits and Cigars, a perfect place to pick something up to indulge in later in the night after exploring lively downtown Portland.

Kennebunkport, Maine : Lunchtime Culinary Walking Tour

5. Kennebunkport, Maine : Lunchtime Culinary Walking Tour

Discover the area that has been home to those who make their living on the sea for centuries. Visit a popular destination for visitors who love history, beautiful beaches, and plentiful outdoor activities. Explore the culinary scene that In recent years is attracting visitors with nationally renowned chefs, gourmet catering companies, craft brewers, and award-winning food artisans. This tour takes a leisurely half-mile walk from Dock Square across the bridge into the lower village as you taste all along the way what it means to be from Maine.  You will visit with shop keepers and food artisans, taste chowders, lobsters, and more, all regionally sourced and created by local talent. A friendly and knowledgeable guide will take you to several venues to sip, taste, and learn about Maine’s culinary history and vibrant food scene. This experience actively works with gluten (not celiac), seafood, nut, and vegetarian dietary preferences and sensitivities to the best of our ability. Guests may pick and choose their participation for any further food issues.  While tours vary, your foodie experience may include, Satellite donuts, fresh lobster right off the boat, Maine clam or fish “Chowdah”, craft-brewed ales or fruit sodas, Maine honey wines, the original Maine whoopie pie, freshly roasted coffees with local roaster and macaroons, and a visit to a summer stand for ice cream.

Boothbay Harbor: 3-Hour Foodie Walking Tour

6. Boothbay Harbor: 3-Hour Foodie Walking Tour

Taste your way through Boothbay Harbor, Maine during this 3-hour culinary walking tour. You’ll learn about the history of Boothbay, its harbor, and lobstering and fishing industries. You will also discover the harbor's award-winning aquaculture and sustainability practices.  Begin your tour with a Prosecco toast as you set off on a mile-long adventure. As you walk along the harbor, you will make stops at a selection of restaurants, bakeries, and gourmet shops, tasting the local seasonal flavors. Enjoy items such as local cheeses, lobster specialties and local oysters.  This is a great way to start your visit to Boothbay, as you will also receive recommendations from your guide for all sorts of activities to enjoy during your time here.

Portland: Old Port Seafood Lovers Tour

7. Portland: Old Port Seafood Lovers Tour

Explore Portland’s vibrant working waterfront to view lobster boats often unloading their catch, learn about the historic wharves and their relationship to the sea. Visit a mix of Old Port and waterfront district destinations, and sometimes a locale or two on the fringes, for a progressive lunch. Servings vary from dine-in and to go from restaurants, pubs, markets, and artisanal shops. Learn about the life of lobsters dwelling on the ocean floor and hear about how hardy lobstermen and women haul in their catch year-round, rain, snow, and shine.

Kennebunkport: 2-Hour Historical Walking Tour

8. Kennebunkport: 2-Hour Historical Walking Tour

Step into the quiet neighborhoods of the first residents during this 2-hour guided walking tour through the historic district of Kennebunkport, Maine. Learn from your local guide about the interesting history of the town as well as amusing anecdotes from the days of being a flourishing shipbuilding town. The tour begins at the Dock Square and will immediately take you back in time to the thriving shipbuilding days of Kennebunkport, Maine. Stroll along Maine Street and weave your way through side streets, seeing the homes of the shipbuilders and merchants of the late 18th and early 19th centuries. Your expert guide will tell you the fascinating history, fun stories, and interesting facts of the area. Learn how “Poor Arundel” as it was known in 1743, become one of the wealthiest towns in Maine by 1810 and what happened at the Customs House during the shipbuilding era in the 1800s.  The tour ends back at Union Square, bringing you full circle. A local treat will be provided to sweeten the rest of your day in Kennebunkport.

Kennebunkport: Historic District Walking Tour

9. Kennebunkport: Historic District Walking Tour

Visit a traditional New England town and get transported back to the 18th century on a lovely leisure walk. Join a local expert on a guided stroll through the historic district to learn about the traditional homes and the many public and private gardens. Take in the quaint facades of sea captains' homes dating back to 1798 while your guide shares stories of the former residents of Kennebunkport. View the public gardens maintained by the Seacoast Garden Club as well as private gardens and hardscapes meticulously cared for by their owners. Hear stories of the past and present gardens while discussing all kinds of botanicals, shrubs, trees, and flowers. End your walk with a visit to 'Ganny's Garden', fashioned after a needlepoint carpet and dedicated to the late First Lady Barbara Bush.

Bar Harbor: Historical Guided Walking Tour

10. Bar Harbor: Historical Guided Walking Tour

Begin this 2-hour walking tour at the clock on the village green. Once here, enjoy a bottle of Maine spring water and meet your local tour guide.  Set off on your you of this fascinating, historic town. Your local, experienced guide will share highlights and secrets from the Gilded Age, as you wind your way through the village. Listen to stories of rum running, and tales of the town folk who influenced the development of Bar Harbor. Stroll along West Street, where the birth of tourism began in this beautiful coastal town and walk through the cemetery before visiting the civil war monument. You will hear tales of John D. Rockefeller, the Great Fire of 1947, and so much more. Return to the village green where you can tuck into a local dessert to finish up the tour.

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What people are saying about Maine

I took my parents on this tour to get to experience Portland like a local and it did not disappoint! Our guide, Ross, was very knowledgeable in Portland’s history and even sang us a few ole’ Portland songs. We learned so much and had a wonderful time. The delicious cookie at the end of the tour was the icing on the cake. I highly recommend this tour if you’re in Portland for a few days visiting or even if you’re a Portland local…anyone can learn from this tour!

It was amazing! so much fun and interesting, Ray S. did such a wonderful job explaining everything about Maine and other history. Very intelligent and funny. We highly recommend this tour :)

Marcia was a great host. It was only two of us but they held the tour anyway and made it an even more special day for us.

Very knowledgeable and personable guide; enjoyed very much!

It was really fun and interesting to see the city!