2026 Benny 500

Berkshire Mountains Tour

June 23rd - 27th, 2026

**REGISTRATION OPENS 9/30/25**

Get ready to rev your engines for the 2026 Benny 500 Berkshire Mountains Tour! This isn't just a drive; it's an immersive journey through charming towns, past world-class cultural attractions, and along stunning scenic byways, promising an unforgettable adventure for every car enthusiast and nature lover. Leave the planning to us and our Concierge team! We will take care of the meals listed, accommodations, directions and entertainment! The only thing you have to do is drive! Don't miss out on our second annual Benny 500.

**15 car max - registration is open for cars 25 years and older

$4,500 includes 2 people /$5,000 family of 4

$2,500 deposit due at registration, remainder due 5/1/26

Tour Includes:

  • 5 Breakfasts

  • 3 Lunches

  • 2 Dinners (including beer and wine)

  • Overnight accommodations

  • All entertainment paid for (museum entrances, activities, etc)

  • Tour Guidebook with area information, route maps, turn by turn directions and mileage

  • SWAG

  • Trouble Truck & automotive tech support (if needed)

Itinerary for the Benny 500: The Americana Tour

Day 1: A Journey Begins

Your adventure kicks off at Parker's Packards with a delicious brunch and our official Driver's Meeting. We'll then hit the open road, letting our classic cars lead us on a scenic cruise through the winding back roads of Massachusetts. Along the way, we will have a chance to step back in time as we visit one of the Berkshires most incredible architectural attributes, The Mount. As the day winds down, we'll gather for a hearty Welcome Dinner (complete with Apple Pie) and settle into our accommodations—a stay in a town right out of a Norman Rockwell painting.

Day 2: Peaks and Paintings

After a relaxing breakfast, we'll bring our beautiful old cars to the summit of Mount Greylock. There, we'll enjoy a scenic picnic lunch with a view that stretches for miles. Later, we'll immerse ourselves in American history and art as we tour the Norman Rockwell Museum featuring iconic Americana paintings.

Day 3: The Mystery Mile

Wake up to a hearty breakfast and prepare for a day of pure surprise! We have a special, mystery adventure planned just for you, complete with a fantastic lunch to fuel the fun.

Day 4: Just Kidding Around

We'll start the day with breakfast before traversing back toward Central Massachusetts. Along the way, we'll stop for some activities designed to make you feel young at heart. As our journey nears its end, we'll come together for a Journey's End Dinner, sharing stories and making memories.

Day 5: Cookouts & Classics

After one last breakfast, we'll make our way to an incredible historical location for the grand finale: the Parker's Packards Cookouts & Classics. This is where our epic tour concludes with an unforgettable BBQ feast, celebrating our shared passion for timeless cars and great company.

Cancellations:

Deposit is due upon confirmation of Benny 500 Tour; Full payment required 7 weeks prior to event (5/1/26). Cancellations 45-30 days prior to start date forfeit the deposit. Cancellations within 30 days of the start, forfeit the total amount.

Please make checks payable to:

Bennett Automotive Foundation

Once you complete the form, please mail checks to:

120 River Road

Rutland, MA 01543

**remainder ($1,500) due by 5/1/26