These Mysterious Hills 'Macabre Pittsfield' October Walking Tours

12:59PM / Friday, October 02, 2026Print Story | Email Story

PITTSFIELD, Mass. — Journalist Joe Durwin offer four walking tours looking into the city's darker past.

Reserve your tickets by emailing info@berkshirehomehistory.com. Visit TheseMysteriousHills.com for more info

City of the Dead: Pittsfield Cemetery

Oct 10, 17 & 30 at 6pm - $10

"City of the Dead" will explore fascinating and tragic stories from some of the more obscure lives of those buried here. It will also lay bare the darker history of the place itself: the vandalism, assaults, exhumations, reinterments, and tragic deaths that have taken place within the cemetery itself.

Ghosts of the Gilded Age: Downtown Pittsfield

Oct 16 & 24 at 6pm

Explore ghoulish legends of the historic Park Square district and a glimpse into Pittsfield in the Gilded Age. An easy stroll around several iconic houses, venues, and other important buildings of downtown.

Dark Origins- 1800s: Downtown Pittsfield

Oct 24 at 8pm - $10
A walk back in time through the dirt and cobble-stones of early Pittsfield, past its burial grounds and nefarious saloons, its brothels, opium dens, and grisly crime scenes.

Roaring 20s: Downtown Pittsfield

Oct 25 at 6pm - $10

From forgotten LGBT history to bootlegging, jewel heists, serial murder, and the rise of the KKK, this walk chronicles the decade that set the tone for a whole century.

These Mysterious Hills began in 2004 as a regular column in the Advocate Weekly newspaper, and has become an archive of obscure Berkshire county history, with walking tours and other special events offered regularly since 2015.

iBerkshires.com Text Ads

rk MILES Blding Materials

Are You Ready to Update Your Home? Start With rk MILES. 4 Locations (800)670-7433

www.rkmiles.com

Save & Earn with Greylock

3.30% APY 6-month certificate. Click to learn more! Insured by NCUA.

www.greylock.org

If you would like to contribute information on this article, contact us at info@iberkshires.com.

Pittsfield Considers Repairing East Part Cemetery

By Brittany PolitoiBerkshires Staff
06:57AM / Friday, October 02, 2026

PITTSFIELD, Mass. — The Historical Commission will consider grant opportunities for repairs to East Part Cemetery.

A resident reached out to the city with concerns about degradation in the half-acre burial ground at the top of Williams Street. East Part Cemetery was established in the early 1800s and has about 300 interments.

“It's a nice old cemetery, and basically, (the resident) had had concerns that the stone wall had taken some damage, the gravestones have taken some damage, and was wondering if there's anything that could be done to repair the gravestones and the wall," City Planner Kevin Rayner told the commission on Monday.

In cooperation with cemetery leadership and residents, the Historical Commission will consider applying for Community Preservation Act funds to support repairs. West Part Cemetery, on the other side of Pittsfield, has previously used CPA funds for revitalization work.

The 1080 Williams St. property is owned by the city and managed by the Pittsfield Cemetery Commission. Rayner presented photos of broken and overgrown gravestones, parts of the stone wall collapsing, and knocked-over obelisks.

Some aspects could use general maintenance and restoration, he observed.

According to the Pittsfield Cemetery and Crematory's website, East Part Cemetery was established around 1808 on land owned by Nathan Webb, who permitted and authorized its use as a public burying ground.

In 1842, Nathan Webb's son, also named Nathan Webb, deeded the property to the Methodist Episcopal Society of Pittsfield as a public burying ground, and in 1893 the Trustees of the Methodist Episcopal Society transferred their control of the cemetery to the Proprietors of the Pittsfield Cemetery. Their action was confirmed by the Berkshire Probate Court.