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Pittsfield Airport Hosts WWII Planes

By Tammy DanielsiBerkshires Staff
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World War II veteran Joseph Whalen waves from the cockpit of a B-25.
PITTSFIELD — The two aircraft circled the field at Pittsfield Municipal Airport before swooping out of the gray skies to rumble down the runway. Propellers spinning, the antique bombers joined two other World War II planes that had landed earlier as hundreds gathered at the edge of the field eagerly snapped photos.

Joseph Whalen waved from the cockpit of the B-25J Mitchell dubbed "Tondelayo." "That's 66!" he yelled out as the crowd cheered.

Whalen, 85, of Tyringham, flew 65 missions over Europe during World War II as a radio operator in a B-25. He and a handful of special guests drove down to Bradley International Airport in Connecticut on Wednesday morning to hop a flight back with the "Wings of Freedom," a flying museum of military aircraft.

"This was really unbelievable," said Whalen. "We got a chance to fly formation with the B-24. That was something in itself just to have the old warbird out sitting on your wing."

Wings of Freedom has been flying into Pittsfield most every other year since 1990. The last time was in 2006, said airport manager Mark Germanowski.


Bernie Trombley looks out of the B-24 after landing in Pittsfield. At right is a P-51 Mustang.
Jean Porter, whose husband, Tom, has been instrumental in organizing the tour's stop in Pittsfield, recalled that first year two of the big bombers had flown in — and the World War II veterans who lined up to the see the planes land.

"The tears were coming down from their eyes just hearing the sound [of the engines]," she said. "Can you imagine 50 of them flying overhead? It must have been something."

This year was the first time four planes had been flown in, said Tom Porter. In addition to the B-25, there is a B-17G Flying Fortress, a B-24J Liberator and a P-51C Mustang.


The nationwide tour is operated by the Collings Foundation, which has been organizing living history events for three decades. Porter got involved because of an uncle who had flown in a B-24 during the war and knew Robert Collings, the museum's founder. The museum was refurbishing the B-24 back in the '80s and had originally named it in honor of the "All-American" — Porter's uncle's plane.

The Wings of Freedom tours 120 cities a year, said James Harley of the Collings Foundation, preserving both the planes and the history of those who flew them. "We want to make sure their memory is kept alive."

This museum offers visitors not only a glimpse into the past but a chance to experience a little of what it may have been like to rumble through the skies over Europe or the Pacific. It's not cheap — 30-minute flights range from $325 to $2,200 (for the Mustang) — but certainly unforgettable.

"Anyone who rides on these airplanes say it's an experience they will never forget," said Porter.

For Bernie Trombley, it was the "flight of a lifetime." The Lyons Aviation mechanic had helped fix the engine on the B-24 two years ago; that earned him a seat on this year's flight of the "Witchcraft."

"It was loud and breezy," he said, but it was worse for the original flight crews who would have stood throughout the missions in temperatures that could plummet to 30 below.

The crews had barely got the planes stored and ready for tours when the skies opened up and the rumble of thunder, not engines, could be heard across the field. Spectators scurried for their cars, cutting the afternoon exhibition short. But the planes will be in Pittsfield until noon Friday, when they will take wing for their next destination. 

Ground tours of the aircraft will be available through Friday morning for donations of $12; $6 for children under 12.
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Gov. Maura Healey's State of the Commonwealth 2026

Gov. Maura Healey's State of the Commonwealth address as prepared for delivery on Jan. 22, 2026, at the State House.
 
Good evening, Massachusetts! Senate President Spilka, Speaker Mariano, who I know is watching from home, Leader Tarr, Leader Jones, and everyone in the Legislature: Thank you for our work together. 
 
We also have empty seats in the Chamber tonight, members of this body who we lost this year. Senator Edward Kennedy and Representative Ann-Margaret Ferrante: Great public servants who served with passion and dedication and will be deeply missed. 
 
Thank you to our Constitutional officers, members of the judiciary, and Governor's Councilors. Thank you to the former governors joining us tonight, Governor Bill Weld and Governor Mike Dukakis. Mayor Wu, and all our mayors and local officials: You'll always have a partner in the Healey-Driscoll administration. 
 
And speaking of Driscoll, let's hear it for our lieutenant governor. Kim, you're the best teammate in government and on the pickleball court, too. 
 
Let's hear it for our friends from labor and all the workers who keep Massachusetts running every single day. Let's hear it for members of the business community, the innovators, researchers, and entrepreneurs who are creating those jobs. Thank you to our faith community who offer support and guidance in a time when people are feeling a lot of anxiety, fear, and uncertainty. Joanna, and our families, thank you for your love and support. Members of our military, veterans and Gold Star Families: everything we have, we owe to you. Thank you. 
 
This year, America celebrates a milestone: 250 years since our founding. Massachusetts, that story began here. That's because people of Massachusetts put everything on the line to fight for what they believed in. Farmers, carpenters, shopkeepers, tavern owners — they stood up with fear and uncertainty, but also with courage and resolve. They set in motion a Revolution that gave us our country and changed the world. 
 
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