Top Cape Cod Historical Tours

Experience the best of Cape Cod in your own time without overlooking any sights with this self-guided driving tour. Download the app with its GPS map, audios, and text, and hit the road from the Cape Cod Visitor Center. Follow the route to see and learn about the peninsula's lighthouses, beaches, and sights, and take optional detours to relax, hike, or delve deeper into the cape's history. For lifetime access, you can dip in and out whenever you wish.

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!

Step into Cape history with a visit to Highland Lighthouse—Cape Cod’s oldest and tallest lighthouse, proudly standing watch over the Atlantic since 1797. Once a critical beacon for mariners navigating the Outer Cape’s treacherous shoals, it remains an active aid to navigation and a beloved symbol of maritime heritage. Join us for an unforgettable stop in Truro, where you’ll have time to: - Climb the lighthouse tower for sweeping coastal views - Explore the keeper’s house and onsite gift shop - Visit the Truro Highland Museum, featuring local maritime history, Edward Hopper’s Cape Cod connections, and stories from the area’s earliest tourism - And enjoy a scenic drive to and from the Lighthouse Whether you’re a lighthouse aficionado or simply love coastal history, this experience offers a rare glimpse into the life and legacy of Cape Cod’s rugged shoreline. Lighthouse and museum admission included in the tour price.

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.

Discover Provincetown from a new perspective with our Private Open-Air Pedicab Tours. Relax in comfort as our knowledgeable guides lead you through the charming streets and scenic coastline of this historic town. Enjoy unobstructed views and personalized insights into local history, culture, and hidden gems that only a pedicab can offer. Whether you're captivated by the natural beauty or intrigued by Provincetown's rich heritage, our tours provide a unique and eco-friendly way to experience all that this vibrant destination has to offer. Unlike large bus or group tours, pedicab tours provide an intimate experience with a knowledgeable driver who can tailor the time to your interests. You can ask questions, engage in conversations, and make specific requests. Pedicab tours can be customized to your preferences and schedule. Choosing a pedicab tour contributes to sustainable tourism practices and minimizes your carbon footprint.

Toast to Provincetown’s vibrant past on history journey down Commercial Street, blending craft cocktails, local bites, and tales of bohemian spirit. Ideal for cocktail lovers and history buffs, this tour celebrates Ptown’s maritime, artistic, and LGBTQ+ legacy. Start at The Harbor Lounge sipping a cape Cod Blueberry vodka lemonade martini amid nautical relics and beautiful harbor views. Pass Lobster Pot, Gov. Bradford and the Old Colony Tap Room one of America's oldest bars. Stop at Spiritus Pizza, tied to the 1990 gays rights riot for two pipping hot slices. Pause at Lopes Square’s 1801 anchor. See Cannery Wharf Park’s harbor views. Catch UU Meeting House’s 1847 steeple. Pass Provincetown Library’s schooner. Wave at A-House (1798), loved by Tennessee Williams. Stop at a local favorite for a delicious fresh Espresso Martini. End at Boatslip Resort’s Tea Dance originating in the 1970's

Explore the highlights of Cape Cod’s seashore, starting from Pilgrim Landing and later into the Beech Forest for a guided hike on this small-group tour. This is an intimate group, so you can ask any questions from your knowledgeable tour guide, and learn all about the area’s history as you explore together. Drive for part of the tour, and then be prepared to walk around one mile (1.6 kilometers).

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 :)

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.

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.

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.

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.

Explore Provincetown in a unique way with this private, 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 there are no reservations needed.