
Thank you to everyone who rented with us in 2025, it was a great season with some amazing photoshoots, beautiful Brides and handsome Grooms, also lots of smiles from our driving rentals !
We'll be back in early spring 2026 after we complete a little winter maintenance.
We are still here answering emails and taking bookings through the winter. So if you want to get in early or buy a Gift Certificate for next year, feel free to drop us a message.
Our driving experiences begin at our home in beautiful Woodstock, CT, where we will describe every detail of your car and any quirks to ensure a trouble-free day. We can recommend our preferred scenic local driving routes and favorite places to stop and enjoy a picnic at sunset. Just want a taste of open-air motoring? We also offer 1 hour taster experience at a specific location for you to drive one of our cars. Get out on the open road for one hour with the wind in your hair, return with a smile on your face, and a passion for our cars. Check out our Instagram & Facebook for updated events and locations where we’ll be.
Getting married or engaged? If you want to arrive in style, or just want to have fun and impress your future bride to be, we offer a variety of rental packages from which to choose. We will ensure all rental agreements and license checks are completed weeks before the event and that all drivers are comfortable with a standard transmission. If it's your big day, you get our undivided attention, we will be discreet but on hand if you have any issues and to assist your florist decorate the car if required. We will also always have a backup vehicle available for the day, just in case.
Weddings, proms, parties, grand openings, benefits; a classic car makes an excellent back drop for a one-of-a-kind photo booth prop. We can even recommend wonderful local photographers and decorate the car for your theme and needs and provide props as well. We also offer services for television, film and advertising shoots.
Drivers must be over 25 and hold a clean US driving license.
You can book direct if you have your'e own auto insurance which covers rental cars
If you need to purchase insurance, or hold a none US drivers license please follow our links to make the booking with Driveshare.com .
Must be named on your policy or have their own policy and also be over 25 with a current US drivers license. They can also be added to your'e Driveshare booking.
We have the same requirements for wedding rentals, however, we will work with you to ensure we have all your details a few weeks before, so there is no extras to think about on your big day..
For your safety we do not offer end of evening getaway cars and normally schedule pick-up around 6pm.
All rentals end at Sunset
Please do not use our vehicles on highways
Please respect our cars and treat them gentle
Ensure you are confident with a standard transmission before renting
Be aware you are responsible to return the vehicle in the same condition as when it was collected /delivered.
Most of all, Enjoy the driving experience !



Charged at $3.50 per mile from our location in Woodstock CT. Delivery is available throughout New England.

Our home in Woodstock, Connecticut is the prime place to discover the road less travelled. Classic Country Drives provides the opportunity to adventureseekers to ditch the modern, rent a classic car, and experience local eats and activities. Meet Samuel Booth, owner of Quiet Corner Classics LLC, Automotive adventurer and retired Super yacht captain, who has spent the last 18 years crossing oceans and planning itineraries in exclusive locales around the world for prestigious clients. Sam has made his home here in the Quiet Corner of Connecticut to bring you the excitement of the open road, the wind in your hair, and no cares in the world.


Not sure if we're the right fit for your needs? Give us a call, and let us know the details of your trip.
Call: 860 336 6549 Email: info@classiccountrydrives.com
Open today | 09:00 am – 05:00 pm |
Monday - Friday: 9am - 5pm
Saturday - Sunday: 8am - 7pm