Top Maine Walking Tours

Dive straight into Portland’s working waterfront—where the smell of the sea, and the bustle of the wharves, set the tone for an unforgettable walk through the city’s past. This immersive experience blends local history with maritime culture, offering a deeper look at how Portland grew from a rugged seaport into one of New England’s most vibrant coastal cities. As you stroll the cobblestone streets and working wharfs, your guide will share tales of shipbuilders, merchants, fires, and fishermen who shaped Portland’s story.

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Avoid the tourist traps and taste Portland, Maine's best donuts on a small-group walking tour. Follow your guide around the Old Port and sample several hand-picked donuts at award-winning bakeries with coffee or water included. Walk a scenic loop while hearing stories of Portland’s history and the invention of the donut. This tour offers a flavorful mix of food and local tales, perfect for food lovers and families alike.

Gain an insight into the history and early residents of Kennebunkport on this guided walking tour with a small group of just nine travelers. Escape the crowds of the Lower Village and follow your guide around the Historic District. Admire the houses where the first residents lived, with the possibility of entering some historic homes.

One hour walking tour - pirates, sardines, and a captured city - the history of Eastport and how life has changed in Downeast Maine. Leaving from the cruise pier, the tour will cover the downtown area of Eastport, stopping along the way for views of historic buildings, sweeping ocean views, and evidence of industries from long ago. Learn about the different fishing industries that shaped the town. Join this tour of downtown Eastport and learn about what makes this coastal village unique and how it's been important throughout history. The tour will meet and end near the cruise ship terminal making it perfect for those coming to port. We will stop for great views of the waterfront and your local guide will teach you about the way of life in Downeast Maine. This one-hour tour is a great opportunity to learn a little bit about the area and get recommendations from your guide about how to spend the rest of your time!

On this smartphone-guided adventure, you'll see Portland’s historic streets and discover its stories. Go at your own pace, anytime. The tour never expires. The tour is professionally produced with pro narration and music. It's location-aware walking step by step through the city. You’ll see the cobblestones streets, wharf street, Henry Wadsworth Longfellow’s home, stops on the underground railroad, city hall, exchange street, the lobster square, historic buildings, and the best spots to eat, including the best donut shop ever. Really, it’s that good. You'll hear the stories of Portland, Anna Kendrick’s favorite hangs, Longfellow’s history, stories of lighthouses, adventure, prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, colonial times, and much more.

Join us on a small group tour of scenic Bar Harbor, ME. The tour will start at the Village Green Park in the center of downtown. We will cover much of the downtown area, highlighting some of the most notable residents and what life was like long ago. Starting with the long history of Wabanaki summer stays, talk about early English settlements, and explore how the Hudson School of Art brought Bar Harbor to the attention of many. The tour typically last between 1 - 1.5 hours depending on the participation of you! Most of our tours are between 2-4 people, giving you a personalized experience you will not get anywhere else! Learn about the real Maine beyond the island and what it's like to live in this unique part of the world. In case of inclement weather, we will reach out 24hrs prior if the tour will be cancelled or changed. In the case that we decide to not run the tour, full refunds will be issued.

Explore the rich maritime history of Kennebunkport, Maine, on this small group walking tour. Discover how this charming seaside town evolved from a humble shipbuilding settlement to a renowned summer destination. As you stroll through Dock Square and the picturesque streets, experience the fascinating stories behind the town's bustling shipyards, the people who lived here, and the rise of present day Kennebunkport. Perfect for history enthusiasts and curious travelers alike, this tour provides an insider’s perspective on the cultural heritage of Kennebunkport. - Walk through the scenic streets of Kennebunkport and hear captivating tales - Learn about the town's transformation from shipbuilding to a tourist haven - Ideal for history buffs, families, and those seeking local insights - Tours available from May to October, offering a unique view of the town's past

Strange tales from haunted homes and hotels abound as does mysterious maritime history. The supernatural stories of this community feature roaming spirits, Spiritualist seances, and a poltergeist. You'll also see the supernatural side of celebrities who summered in the Kennebunks, including Booth Tarkington and Margaret Deland, and fathom the seafaring yarns of haunted lighthouses, dire premonitions, ghost ships, and sea serpents.

Experience Acadia National Park’s scenic Ocean Path with this self-guided walking tour. Look out for the variety of marine wildlife. See the breathtaking foliage and uncover the booming Thunder Hole. Hear stories of shipwrecks and devastating fires. Finally, take in the views from scenic Otter Point Outlook. Purchase one tour per car, not per person. Everyone explores together! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

On this walking tour, we’ll explore the city’s significant role in the Underground Railroad and the individuals who helped shape its fight for freedom. The tour is self guided on our walking tour app. It's hands free, plays as you walk and you can go at your own pace, anytime, it never expires. You’ll walk through historic streets where ordinary citizens took extraordinary risks to assist those escaping slavery. We’ll visit former homes, churches, and workplaces that served as safe havens and meeting places for abolitionists, reformers, and community leaders. Each stop demonstrates how Portland’s waterfront and neighborhoods became centers of courage, compassion, and quiet resistance. Let’s start our journey at the Mariner’s Church Banquet Center, a landmark that saw both Portland’s growth and its dedication to justice.

Learn about Portland's history with this walking tour, which will take you through the Old Port, downtown, and waterfront areas. You'll see all sorts of historic attractions, including the home of Hendry Wadsworth-Longfellow, the Eastern Cemetery, and the Abyssinian Church, all with a professional guide on hand to share stories about the city's past.

Submit yourself to the spooky stories of Bar Harbor on a unique night walking tour that details the coastal city’s ghostly leanings. Led by a local paranormal expert, you’ll stroll the town stopping at haunted landmarks such as Agamont Park, Bar Harbor Inn, Criterion Theater, Bar Harbor Club, and along Main Street, hearing ghost stories, history, and other lore that brings the city to life.

Ditch the standard sightseeing itinerary and indulge in stories of the strange, supernatural, and macabre during this evening walking tour through Portland’s historic Old Port district. Listen to ghost stories from your guide as you take in the picturesque waterfront and historic waterfront, including mysterious apparitions and a sea serpent named Cassie.

Weird tales include the strange goings-on at Boothbay Harbor's famous Opera House, a wealth of haunted B&Bs, and several other supernatural hotspots about town. We also introduce you to the compelling mystery of the Lady of the Dusk. Who was she? And what do the numbers scribbled on a strange note found on her body mean?

The Boos and Brews Walking Ghost Tour uncovers Boothbay Harbor’s unexplained past with eerie events told from a local’s perspective. We combine spine-tingling tales told in picturesque locations with a visit to the Footbridge Brewery for craft beer and barbeque! A local paranormal researcher tells ghostly tales about the harbor’s most haunted old sea captain’s homes, Boothbay Harbor’s very own sea serpent, and the spooky legends that surround many of the harbor’s islands. We’ll wrap up our walk on the weird side at the Footbridge Brewery where you can enjoy beautiful harbor views along with a craft beer flight, brewed with all locally sourced Maine ingredients, and Bridge House barbeque. Unlike national corporate chains, Mysterious Harbor Tours is locally owned and operated. No mega-groups of 30+ people. Enjoy an intimate, creepy atmosphere where you can actually hear your entertaining guide.

A historic coastal Maine town, a classic national park: this self-guided experience gives you an opportunity to experience both the city of Bar Harbor and Acadia National Park. You’ll download a tour guide app that provides both a walking tour of Bar Harbor and a driving tour through nearby Acadia National Park. Follow the loop around the park then explore Bar Harbor’s history as you pass by centuries-old buildings.

Discover the vibrant history of Portland’s Old Port on this engaging walking tour. Wander through cobblestone alleys and merchant blocks rich with stories of sailors, reformers, and immigrants. Learn about the Portland Freedom Trail, which honors the city’s fight for freedom and civil rights. The tour showcases the Old Port’s architectural charm and its transformation from a bustling shipping hub to a cultural center. Experience the tales of resilience embedded in its streets, from the Great Fire of 1866 to the revitalization efforts of the 1970s. Join fellow history enthusiasts for a memorable journey through Portland’s past and present. — Explore the historic Old Port district, a cultural and commercial hub — Walk along the Portland Freedom Trail, learning about civil rights — Discover stories of resilience, fire, and maritime life — Ideal for history lovers and those curious about Portland's heritage

An excellent tour is so much more than a checklist of stops or stories. We will create a meaningful experience you'll cherish as we explore Acadia and the many hidden gems just outside of the national park on a half-day adventure tailored specifically to your group. No rush, no crowded bus. Just you, riding in comfort with guides who never tire of sharing our island. We'll handle the passes and driving, leaving you free to really enjoy Acadia. We know the secrets to escaping the press of crowded areas, while ensuring you don't miss a thing. Our guides thrive on adjusting tours to match your group's interests and abilities. A great tour leaves you brim-full of the magic of this lovely place. Sure, there are stories, tour guide puns, pictures to take, history and trivia you might forget.. but mainly, that feeling of really experiencing this place in a special way. You will leave, knowing you saw and felt more, with less stress, than anyone choosing to explore without a local expert.

Explore the beauty and history of Portland with this combo of a walking and driving tour. Dig deep into the city’s history as you stroll down cobblestone streets and admire old brick architecture by the waterfront. Visit bustling neighborhoods like Old Port and the Art District, stop at shops and restaurants whenever you please, and breathe in the coastal air. Then take a drive out to the east and west promenades, before swinging down to the famous Portland Head Light lighthouse. It’s the most comprehensive way to experience this unique, quirky city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Stroll through Bar Harbor with a small group on this tour focused on the local cuisine. As you walk, listen to in-depth commentary on the local food scene and stop for tastings at establishments around the Village Green. The tastings add up to a satisfying lunch, and the small group size means you'll have plenty of personalized attention and chances to ask questions.

The most immersive way to see Historic Portland is on foot. Our 1 hour 15 minute walking tour takes you down the cobblestone pathways of our historic city in search of spirits that linger from times long past. Our knowledgeable guides will enchant you with tales of Portland’s most renown ghosts as well as the area's vast and rich history. You’ll hear fascinating and spooky tales from the first European settlement in 1632 right up to the present day. Discover the many times Portland has fallen and risen anew, and hear about the restless spirits who remain, unable or unwilling to move on. Follow our guides as they lead you by lantern-light sharing the ghost stories, legends, and folklore of this beautiful city.

The Boothbay Harbor Bites guided food tour is a carefully curated, unique culinary experience featuring five beloved, locally-owned restaurants and specialty shops designed to give you a taste of what it means to live and eat in this historic New England fishing village. Join our friendly, local tour guide on this movable treat feast along the harbor where you’ll hear stories about Boothbay Harbor while enjoying mouth-watering savory samples and sweet bites with opportunities to shop and take photographs.