Top Cape Cod Walking Tours

Discover P-town's LGBTQ+ sites, oldest gay bars and historic stories. Go at your own pace, anytime. Explore the rich history and cultural significance that have made Provincetown the gayest town in America. Go at your own pace, anytime. Go at your own pace, anytime. The tour plays automatically as you walk making it a hands free heads up spooky experience. The tour is all outside. You can go anytime, 24/7/365. It does not enter any buildings :)

Join Your guide Cathy and embark on a captivating journey through Provincetown’s West End, where the sands of time meet the tides of history. This unique walking tour weaves together the stories of ancient homes, weathered wharves, and steadfast lighthouses, all nestled along the shimmering edge of Provincetown Harbor. Designed to feel like a step into a living museum, this tour blends maritime grit, pilgrim lore, and bohemian charm, offering a soulful exploration of Cape Cod’s northernmost tip. This 90 minute walking tour covers about .5 mile along the West End of Commercial Street. Each stop pulses with Provincetown’s unique blend of history, art, and seafaring spirit, making this tour a love letter to a town that’s both timeless and ever-evolving. After the tour, opt for a Pedi-cab back to the center of town!

Provincetown’s charming seaside facades hide a sinister past soaked in blood, betrayal, and supernatural terror. On this chilling self-guided walking tour, you’ll discover the dark underbelly of Provincetown’s history, from bloodthirsty pirates and treacherous mooncussers who lured ships to their doom. I’ll also tell you about the restless spirits that continue to haunt the town’s historic buildings and picturesque streets. Starting at the infamous American Horror Story house, you’ll journey through Provincetown’s most haunted locations. You’ll explore historic cemeteries where smallpox victims lie in unmarked graves, and pass by former funeral homes that now operate as quaint inns. Along the way, you’ll discover how this seaside paradise earned its ominous nickname “Helltown” after centuries of maritime tragedy and malevolence.

Toast to Ptown’s past on a Commercial Street stroll blending craft cocktails and bohemian history. Perfect for drink lovers and history buffs, this tour celebrates our maritime, artistic, and LGBTQ+ legacy. Kick off at local establisment with a Cape Cod Blueberry Martini. Enter the Old Colony Tap Room, one of America's oldest, most weathered dives made completely from old shipwrecks. Pass the iconic Lobster Pot and Governor Bradford to stop at Lopes Square to see its 1801 anchor, and learn about the old colony railroad. Look up at the UU Meeting House’s 1847 Greek Revival steeple, then head into the Ptown Library to glimpse the grand schooner inside. Pay homage to literary history at the Atlantic House (A-House), a 1798 tavern loved by Tennessee Williams. Next, keep the energy high with a shaken Espresso Martini at a local favorite. Finally, wrap up at the famous Boatslip Resort for the legendary Tea Dance—a disco-fueled, open-air tradition pulsing since the 1970s.

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by a local expert, this 3-hour walking tour features multiple tasting stops with hand-picked seasonal bites from beloved local spots. It’s a delicious way to explore the area, whether it’s your first visit or your summer tradition. Along the way, hear the stories behind the food—tales of tradition, local legends, and the people who make Chatham so special.

Explore Provincetown's rich history with this self-guided walking tour! Discover the charm of Commercial Street, admire the towering Pilgrim Monument, and visit the bustling Beachcombers at Town Hall. Stop by the historic Adams Pharmacy and Whalers Wharf. Take in the architecture at 2 Masonic Place and the Martin House. Experience the legacy at the former Zora's Fish Market and Railroad Wharf. Pass by the Seth Nickerson House and the home of Jack Tworkov. Conclude at the stunning Land's End Inn and Pilgrim's First Landing Park. 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. This isn't an entrance ticket. Check opening hours before your visit. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want.

Herman Melville said this city was perhaps the dearest place to live in, in all of New England. On this tour you will explore the streets that inspired Melville's tale, showcasing the city's nineteenth-century architecture and the landmarks that played a crucial role in both the whaling industry and Melville's masterpiece. Go at your own pace, anytime. The tour is location aware and plays as you walk guiding you step by step through the streets. Stop anytime, and listen again later anytime.

The Cape Cod Food Tour offers a delightful culinary adventure through historic Hyannis, where food lovers can savor a range of local delicacies. Stroll along the charming main street and to the picturesque harbor while stopping at only locally owned and operated restaurants and shops and sampling fresh, house-made, local authentic dishes from various restaurants. A fun and knowledgeable guide will take care of everything! They will share stories about the food, restaurants and shops and the owners. You will learn some great facts and history about cape cod and uncover Hyannis' rich history. This tour is ideal for all. explore the local culture through its cuisine and history. - 3-hour guided walking tour showcasing the best of Hyannis food - Sample dishes from renowned local restaurants while learning about the owners and restaurants and food - Ideal for families, groups, friends and couples of any age - Comfortable walking shoes, dress in layers, bring rain gear if applicable.

Ready to taste Ptown? Lace up for a 2-hour trek through history and coastal rebel lore. You’ll track the footsteps of Anthony Bourdain and dive into the bohemian scene that made this fishing village the birthplace of modern American theater. Find out where the Provincetown Players launched, where an undiscovered Eugene O’Neill staged his first plays. Alongside O'Neill, trailblazing writers like Susan Glaspell, Edna St. Vincent Millay, and John Reed fueled the town's creative fire. Over the decades, icons like Tennessee Williams, Norman Mailer, and poet Mary Oliver drew inspiration from the salt air, while acting legends like Marlon Brando and Bette Davis graced local stages early in their careers.End your journey at Vorelli's Restaurant, a beloved local classic. Sit back, relax, and reward your feet with the ultimate Cape Cod feast: a massive, chunky lobster roll, a rich, creamy cup of New England clam chowder, and a refreshing non-alcoholic beverage of your choice and a ice cream cone

Embark on a privately guided journey through Truro’s soul, where history, culture, and breathtaking landscapes converge. This tour weaves together three iconic Cape Cod landmarks: The Highland House Museum, Highland Links Golf Course, and the historic Highland Light. Begin at Highland Light, Cape Cod’s oldest lighthouse (1797). Ascend 69 steps to the lantern room for panoramic Atlantic Ocean views and hear the thrilling tale of its 1996 relocation. Next, step into the Highland House Museum, a 1907 farmhouse-turned-hotel-turned-cultural gem. Once a haven for literary giant Henry David Thoreau, who penned parts of Cape Cod here. Explore rooms inspired by Edward and Josephine Hopper’s artistry. Stroll along the Highland Links Golf Course, America’s first 9-hole links course. Nestled amid rolling dunes and windswept grasses. Available June-September only.

See Provincetown from a viewpoint that most visitors never experience: through the eyes of the infamous 17th-century Anne Hutchinson on this walking tour. With a costumed guide who plays Hutchinson with a gender twist, see the town's landmarks as you hear both traditional and irreverent “heretical” accounts of its history—the latter inspired by Hutchinson’s challenging of the Puritanical mores of her time. With commentary reflecting the “licentiousness” Hutchinson was accused of, the tour content is suitable for adults only.

Walk the cobblestone streets of New Bedford with a self-guided audio tour that plays automatically on your app. Moving between the historic downtown and working waterfront, you will use your GPS to trace the history of a city shaped by ambition, labor, and the sea. Along the way, pass landmarks like the Whaling Museum, Seamen’s Bethel, Mariners’ Home, and Custom House. You will uncover deep history, from Wampanoag coastal knowledge and whale oil fortunes to the abolitionist networks that sheltered Frederick Douglass. Explore at your own pace—pause to take in views toward the harbor or linger along the historic blocks. The audio resumes whenever you are ready, allowing you to move freely without keeping up with a group. This is a self-guided experience (no in-person guide). Download the tour in advance and use it anytime—it works offline and follows your location along the route.

Discover the culinary scene of Hyannis on this walking food tour that takes you through the charming waterfront and historic streets. Sample a variety of freshly prepared dishes from local favorites stopping only at locally owned and operated restaurants and shops . Sweet and savory tastings! All while enjoying fascinating stories from expert guides. Ideal for food lovers, families, and couples looking for a unique dining experience. Comfortable walking shoes are recommended for this appx 3-hour tour covering about a mile. - Enjoy a diverse selection of local foods from Hyannis' best eateries - Guided tour featuring insights into the area's history and culinary culture - Perfect for families and couples, small groups seeking a memorable outing - 2.5-3 hour walking tour with a route that includes both indoor and outdoor stops

Enjoy complete flexibility and explore the parts of Massachusetts that most interest you with this collection of self-guided walking and driving tours. Receive 10 different itineraries and choose the day and time to use any of them. Use offline with GPS and learn about each place as you travel through.

Skip traditional walking tours and explore Provincetown in a unique way with this app-led scavenger hunt. Discover hidden gems, landmarks, and local trivia as you navigate the historic district. Perfect for everyday adventures, bachelorette parties, birthdays, or corporate team building. Choose your interactive role and compete or collaborate with your team. Challenges vary for a personalized experience, and no reservations are needed.

Learn about Plymouth through games on this interactive scavenger hunt. Using your smartphone as your guide, visit different locations and solve puzzles with your team. Enjoy the route at your leisure, as only puzzles are timed. As you enjoy the sights of Plymouth, unlock educational riddles to figure out where to go next.