Doctor Gasp returns to haunt New England with his Misshapen Jack-O-Lantern Tour.

For singer-songwriter Dan Blakeslee, embarking on a walking tour through the state of Massachusetts was a liberating experience.

“I went on the biggest journey I’ve ever been on,” he said. “It was good fun, a really amazing experience I will never, ever forget.”

Blakeslee, a Seacoast native now living in Somerville, Mass., joined fellow musicians Mark Mandeville and Raianne Richards on the tour in June. The three traveled their route by foot, walking eight or nine miles between gigs. Mandeville and Richards first launched the annual tour in 2010, but Blakeslee had never done anything like it.

“We played a lot of nontraditional venues, and that was actually the inspiration to continue doing that instead of doing bars all the time, which is what I’d been doing for years,” Blakeslee said. “I was like, you know what? I want to play more art spaces and living rooms, places where people can actually listen. That’s the most important thing.”

That approach applies not only to Blakeslee, but also to his musical alter-ego, the abominable Doctor Gasp, who returns this month for his most ambitious tour yet. He is playing 31 shows around New England in October, and connecting the dots of each gig on a map forms the shape of a hideous jack-o-lantern. Gasp, you fiend!

“The Misshapen Jack-O-Lantern Tour” makes several stops on the Seacoast, including a pair of shows on Saturday, Oct. 13. Following a slot at the Harvest Festival in York, Maine, at 5 p.m., Gasp will play his annual Halloween special at The Press Room in Portsmouth at 9 p.m. Joining him will be his band, The Eeks, consisting of the heinous doppelgangers of local guitarist Nick Phaneuf, drummer Jim Rudolf, and pianist Mike Effenberger. The tour concludes on Wednesday, Oct. 31—Halloween night—at The Barley Pub in Dover.  

Although the tour includes a handful of bar gigs, Gasp will also rear his beastly head at a number of art galleries, festivals and houses. Since he just moved out of his apartment and put all his belongings into storage, he’ll spend the month as a musical hobo.

“My lease had run out and I didn’t find a place, so I was like, ‘Who cares? I’m going on tour,’” Blakeslee said.

Playing 31 shows in one month is no small undertaking, even for someone who’s been performing live for close to 20 years. But the walking tour this summer helped prepare Blakeslee for the rigors of an intensive tour. On that expedition, he walked up to seven hours per day, with a 40-pound pack on his back, through an oppressive heat wave. He recalled walking up a long, steep incline one day when temperatures exceeded 100 degrees.

“I’ve never been so hot in my entire life. I thought I was going to pop,” he said. “I could not keep awake. It was terrible.”

But enduring such difficulties helped open Blakeslee up to new touring possibilities. Although he’s played more than 1,500 live shows over the course of his prolific career (he tallied up the total last year), he has rarely embarked on extensive tours.

“Going out on tour is like going into the unknown. It’s scary and … intriguing. But it’s really hard to book all that stuff and hope that it really works out,” he said.

It was only after the tour that he decided to pursue the jack-o-lantern route for Doctor Gasp, an idea he’d toyed with years earlier but never expected to pursue.

“I never thought twice about actually doing it,” Blakeslee said. “It wasn’t until I got back from the walking tour that I was like, ‘You know what, I’m doing it.’”

Of course, Doctor Gasp has grown accustomed to a heavy gigging schedule in October. This is the fifth year Blakeslee has donned the Gasp mask, and he plans to record his third Halloween CD, “Vampire Fish for Two,” directly after the tour. He’s already working on some new Doctor Gasp material, some of which he may try out during the tour.

Blakeslee said he’s harbored a special fondness for Halloween since his childhood, when his parents took him to lots of Halloween activities. Stories about the Headless Horseman and songs like Bobby Pickett’s “Monster Mash” have always captured his imagination. Coincidentally, Pickett is a native of Somerville, where Blakeslee now lives.

For all his nefariousness, Doctor Gasp puts on a highly entertaining show, with festive original songs based around old-time cult horror themes. He invokes Pickett, Alfred Hitchcock and John Zacherle to produce haunting but playful folk songs, complete with Blakeslee’s pliable vocals, proficient guitar playing and animated showmanship.

For a complete schedule of the Misshapen Jack-O-Lanter Tour, visit www.drgasp.com.