Wicked Summer Fun Guide

Wicked Summer Fun Guide

Wicked Summer Fun Guide

Photo by Wei Xuechao/Xinhua via Getty Images)

From the people (me) that brought you Massachusetts TOP Clam Shacks, we present Massachusetts BEST Car Shows! No matter what age you are, everybody knows someone, who knows someone who owns a classic car.

We see them almost every weekend in the Summer, all over New England. One, two, three, four, five, six, classic cars driving by you on the other side of the road. You know they must be headed to a car show near you.

How Many People Own A Classic Car?

According to insurance company The Hagerty Group:

The best estimates we have at the Hagerty Group, which sells classic-car insurance, peg the number of collector cars in the U.S. at roughly 5 million, of which 58 percent are owned by baby boomers, or those born from 1946 through 1964. 

How Much Does It Cost To Own A Classic Car?

A website called CarInvestor.com says:

You can expect to pay anywhere between $10,000 and $50,000 for a classic car that’s in good condition. If you’re looking for one of the rarest and most sought-after classic cars, then prices can go into the millions. But there are also plenty of cheaper classics out there to get started with if you’re on a budget.

What’s YOUR Style?

My brother Rich jumped into the world of car shows a few years back. He enjoyed it SO much, he found a pristine used 2005, fire-engine red Ford Thunderbird and bought it! Now, this T-bird, is from the 2005 series. WHY would he buy a 2005 car? Well Ford, discontinued the T-bird the FIRST time in 1997. Then, to prepare for the 50th anniversary, they resumed production with a brand new, retro style starting in 2002. But because of lackluster sales of the new, old, version they stopped, again in 2005. So Rich’s car could be in fact considered a classic, seeing that it was only part of a three year production run.  Ironically, Ford sold only about 50,000 T-birds, celebrating its 50th birthday.

So let’s grab our sunglasses, put the top down, and go find Massachusetts BEST Car Shows! Look for Rich’s cool T-bird too! It’s there!

  • July 9th-Bay State Auto Club

    (Photo by Eamonn M. McCormack/Getty Images)

    This one is BIG! Celebrating 50 years!

    Where: Endicott Estate in Dedham

  • July 15-"Local-Motive" Car Show

    Keith Moon: Classic Images of the Iconic Drummer

    (Photo by Jack Kay/Daily Express/Hulton Archive/Getty Images)

    Where: Laston Memorial Field, Route 7 Lanesborough, MA.

    Proceeds help a local charity too!

  • August 13-Horsepower Vs Horsepower!


    (Photo by Jesse Grant/Getty Images for Paramount+)

    Vintage cars Vs, Horse drawn!! Hahah!!

    What a sight this is!

    Where: Held at the 24th annual Orleton Farm Show in Stockbridge 

  • August 19-Cape Cod Classics Car Club

    (Photo by Mike Windle/Getty Images for SXSW)

    Another BIG one celebrating 29 years! Also benefits a local charity.

    Where: Patriot Square 492, Route 134 South Dennis, Massachusetts


  • September 16-Cannonball Run

    (Photo by Jesse Grant/Getty Images for Gucci)

    This one comes with a live music and a DRIVE-IN movie at dusk!!

    Where: Slo Rollers Drive In Theater, 80 West Street, Westford, Massachusetts

  • NOW! "Saturday Night Cruise-In!"

    (Photo by Jesse Grant/Getty Images for Gucci)

    This is FUN weekly event, each Saturday night now, until 9-23-23.

    Where: Patriots Square, 492, Route 134 Dennis, Massachusetts

    Produced by Cape Cod Classics Car Club

  • 7th Annual "All Corvette Show!"


    (Photo by Bill Pugliano/Getty Images)

    NOW, you have my attention! This is the BIG PAPI of Corvette shows in Western Massachusetts, usually held in May each year. The vette would be my car of choice if I ever jump into this world!

    Where: 440 Hall of Fame Avenue, Springfield

  • Foxboro Jaycees Car Show


    (Photo by Alex Pantling/Getty Images)

    Usually held in June. Next year will be their third! Benefits the Foxboro Jaycees.

    Where: 40 South Street, Foxboro


  • July-13-Cruise Night at Patriot Place!

    (Photo by Bill Pugliano/Getty Images)

    THIS show is actually organized by Patriot Place, at Patriot Place. SO it’s bound to be BIG!

    Where: Bass Pro Shops, 1 Bass Pro Drive, Foxborough

    From the website:

    Join the Mass Cruisers Auto Club for free and exciting Cruise Night at Bass Por Shops Patriot Place!

    The Bass Pro Shops Cruise Nights with the Mass Cruisers are known throughout New England. Bi-Weekly hundreds of cars, owners and fans attend for FREE and enjoy all the sights and sounds of Patriot Place.

  • July 1-First Independence To Cruise Show


    (Photo by Scott Olson/Getty Images)

    Where: Hebert Candies & Gifts 574 Hartford Turnpike Shrewsbury Massachusetts

    You don’t even need to display a car! They just want ya to visit! Proceeds benefit disabled vets. Plus, the Hebert Candy Mansion is a local landmark. It’s actually a mansion full of candy. I wonder if Willy Wonka knows about this place.

  • September 3-Spindles Annual Car Show


    (Photo by Rick Diamond/Getty Images for Country Music Hall Of Fame And Museum)

    Where: Marshfield Fair, 140 Main Street, Marshfield.

    Any chance to visit beautiful Marshfield anytime is fine by me!

  • July 16-Microcar Classic Car Show

    (Photo by Guido De Bortoli/Getty Images for Fiat 500 Collection)


    Larz Anderson Auto Museum
    15 Newton Street
    Brookline, MA 02445
    Wait, MICRO CARS? You can actually RIDE the cars! Website says:
    The Microcar Classic Event is one of the most unique and memorable lawn events at the Larz Anderson Auto Museum AND IT’S BACK IN 2023. Unlike most car shows, where cars have signs asking people not to touch, at this show the owners give rides around the grounds of the Museum. The Museum is hosting this family-friendly car show that everyone can enjoy. For the eighteenth year, sponsored by the Gould Family, the show will feature rides for the kids (with parents approval, of course) in fun cars like Fiats, Messerschmitts, Crosleys, Subaru and many others.
  • July 8-Wentworth SAE Car Show

    (Photo by Mike Windle/Getty Images for SXSW)

    Where: Wentworth Institute of Technology, 550 Huntington Avenue, Boston

    This is a really cool event helping students compete in national competitions. They have a Best of the 80’s Class! Take a look at more from website:

    Fundraiser car show for the Wentworth Society of Automotive Engineers (SAE). We are a student-run organization that competes in the intercollegiate BAJA SAE vehicle design competition. Designing and fabricating a bespoke racing vehicle every 2 years is financially demanding, so any support is appreciated. Come meet the team, check out our garage space, and see our latest engineering projects and race vehicles. Food and drinks will be available on-site. All makes and models are welcome with multiple judging classes. Trophies will be awarded based on different classes.

  • August 12-Adirondack Chair Cruise & Car Show

    (Photo by Tristan Fewings/Getty Images for EON Productions, Metro-Goldwyn-Mayer Studios, and Universal Pictures)

    Where: Sandwich Arts Alliance, 124 Rt 6A, Sandwich

    Organized by the Cape Cod British Car Club. (That’s actually a thing.) Will o07 be there?

    This one features specialty chairs, AND CARS! From website:

    Event is a multi-function day of fun, driving to find 22 amazing artist-inspired Adirondack Chairs, seeking answers to trivia questions, followed by a car show at the Sandwich Arts Alliance with friends and the public.

  • October 7-Brimfield's 15th Annual Auto Show


    (Photo by Nicky J Sims/Getty Images)

    Where: Brimfield Auction Acres, 35 Main Street, Brimfield

    This area is known for all things classic!! This is a 15 year event and going strong!


    The Annual Brimfield Auto Show! Over 26 Categories, 81 Trophies! 3 Best in Show!
    Inviting all antique cars, muscle cars, Classic trucks, Street Rods, custom cruiser classic imports utility vehicles and antique fire apparatus. Car registration opens at 8 am $15.00 per vehicle. Admission for $5 Free for senior Children under 13 free (and military & veterans)

  • My Brother's Cool T-Bird!

    2005 Ford Thunderbird

    Photo by Rich Dowd

    Here’s Rich, my brother, proudly showing off his well deserved toy, his pristine 2005 Ford Thunderbird, with convertible hard top!

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