Top Gloucester Walking Tours

Excellent way to spend the evening and hear and see some of the rumored and spooky tales and places in Glouster. Our guide was very knowledgeable, great storyteller, and a lot of fun to listen to. Her outfit and instruments captured everyone's attention right from the start. Definitely recommended.

Wonderful tour, lovely guide. Besting Salem tours! The guide shares rarely heard stories and designed a fantastic tour. Moderate walking with breaks and more than one spot to be able to sit for a bit. Music and passionate storytelling included!

Salem is a must see! Lots to do, plus ,boston and plymouth, just a short car ride away. Food is great, tons of places to choose from. At night,I highly recommend taking a ghost tour, tons of history!

We used the self audio tours while driving from Concord to Lexington, around Martha’s Vineyard, and Salem, Massachusetts. It worked beautifully and the information was so very helpful in making our visit to these places, a rich one.

Hearing the history of the area at a leisurely pace while driving. Loved the concise history narration.

I used the audio tour in conjunction with the Hop on Hop off bus, so I got the narrative about areas around the stops. No rush, no fuss. It was a good solution and much less expensive then an escorted tour with a bunch of people.

Very fun way to spend an evening! Would highly recommend the tour.

Strongly recommend. The staff for this experience has been giving tours in Boston and Salem for the past 8 to 10 years. Incredibly passionate. Nice to learn about the spooky and weird history of a storied area.

This was really great! The driving tour through Cape Ann was the most beautiful drive I’ve ever been on. The ocean views were gorgeous and the town of Rockport was full of shops and galleries. The Freedom Trail tour was perfect for first time visitors to Boston. Our experience of Boston would not have been as wonderful without this guided tour!

This was such a good experience, I really appreciated the map to show us where to go to follow the freedom trail and the narration was perfect, not too long not too short! This is such a great, affordable alternative to a guided tour.

These are great tours - we did several over our vacation. A little hard to navigate in cities with a lot of traffic. We loves getting the experience of a guided tour but not being stuck on someone else's schedule

This tour was so much fun! Aspen is full of knowledge and makes each story exciting. I want to explore Gloucester more because of what she taught us during the tour. She makes things entertaining and the tour is a good length of time without feeling exhausting. I think the tour is a good price for the amount of fun you have. I'd love to go again!

Loved the Haunted Harbor Walk! Such a fun mix of spooky local lore. Aspen was AMAZING. Her aesthetic totally matched the vibe for the night. New England tales from the crypt delivered harbor side, by the light of a lantern, made it feel authentically haunted. Perfect for a cozy night out with friends or a date. This local, lore loving, witch gives it a 10 out of 10 👻.

👻 ⚓️ Haunted Harborwalk – Chilling Fun in Gloucester!The Haunted Harborwalk in Gloucester is a must. We attended the 9pm tour on October 23, 2025. This isn’t your typical tourist ghost tour — it’s a deep dive into the paranormal history and eerie legends that have haunted this harbor town for centuries.Our guide, Aspen, was a natural storyteller who made the ghosts, sailors, and mysterious happenings of Gloucester’s past come to life. From tales of shipwrecked souls to whispers of witchcraft in Dogtown, every stop had a story that was intriguing.It’s the perfect mix of spooky and historical information. You’ll learn about real local lore, haunted landmarks, and some maritime mysteries that’ll make you look at the harbor a little differently afterward.If you love ghost stories, local legends, and a walk under the moonlight filled with paranormal vibes, this tour is an absolute must-do.

This was such an entertaining tour! Our tour guide, Aspen was very knowledgeable and passionate about the tour. I would recommend this to tour to both locals and tourists looking for some spooky fun!

We had such a great time! I was born and raised in Gloucester, one of the stops was actually in front of my childhood home! Despite being a life long resident I actually learned quite a few new things about this town and its history. The tour guide was amazing! It was not scripted, it was very naturally flowing, she really knew her stuff and made it fun along the way. I highly recommend this as a fun night out, whether you are a tourist or a local.