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Bewitching Boston For October

This blog post was updated on August 20, 2018.

The Puritans founded Boston in hopes that it would be their city shining brightly on a hill, a place for complete religious freedom. A city founded on freedom hundreds of years ago makes for one of America’s best places to visit in October.

The spirits of those who have resided in Boston come out in full force, just as the pumpkins start to appear everywhere.

If you need a travel destination for October, Boston may be it. Visit in order to be spooked, chilled to the bone, and even to pick from a picturesque pumpkin patch. And with plenty of cheap flights to Boston out there, there’s nothing stopping you!

Hang Around Boston Common: Boston Common serves as not just a renowned public park in the city, but also the oldest park in the country. Around nearly 50 acres, you can hang around. Once you discover this area’s history, you might not use the term “hang” loosely here. A number of hangings used to take place in Boston Common, making it a rumored haunted sight in the city.

Navigate Through the Dungeons of Fort Warren: Situated in Boston Harbor, the trip out to Georges Island is well worth it for those who enjoy being spooked just in time for Halloween. Fort Warren lies on the island, a Civil War prison used to house Confederate soldiers in its heyday. Those in town for October in Boston don’t come here for history however, but to explore the Fort’s eerie dungeons. A wife of a former prisoner who came up to Fort Warren to spring her husband supposedly still lingers around the place.

See Where Boston’s Beyond Rests: Boston’s residents who have long since past linger in the many picturesque and chilling cemeteries in the city. King’s Chapel and Burying Ground boasts the oldest headstones in the city, including that of Elizabeth Pain, the model for Hawthorne’s Hester Prynne in The Scarlet Letter. If that doesn’t spook you, Copp’s Hill Burying Ground is the second oldest cemetery in the city. The small plot reportedly houses around 10,000 souls.

Make a Day Trip to Salem:  If there were one place close to Boston that lives and breathes the month of October better than the rest, Salem would be the place. From the Bewitched statue to the popular television show witch-housewife, Nathaniel Hawthorne’s supposedly haunted House of the Seven Gables and the Witch House, Salem comes alive for the Halloween season. The draw to Halloween comes mostly from Salem’s history when in September of 1692, 156 people stood accused of being witches. Witchcraft and being burned at the stake seem to be the theme of this town. Salem’s definitely made it onto more than a few lists of the top halloween destinations.

Visit a pumpkin patch: While you maybe staying right in the heart of downtown Boston, you can still feel the October spirit after visiting a nearby pumpkin patch. Within close reach of the city, hanging out in a pumpkin patch even just for the photo opportunity brings on the Halloween spirit. While there are a number of pumpkin patches in close proximity to Boston, you can check out the website of the Massachusetts Department of Agriculture for complete listings.

Flickr: David Berkowitz

About the author

Suzy Guese

Suzy Guese is a travel writer from Denver, Colorado. She caught the travel bug after taking her very first flight at just three months old—she was headed for Disney World—and has been a total travel junkie ever since. From family car trips across North America to stints abroad in Europe, Suzy travels the globe with her redheaded temperament in search of sarcasm, stories, and travel tips to share with anyone willing to listen. She blogs about her travels at

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