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About

Classic Car Rental

Based in Woodstock, CT, Classic Country Drives is a classic car rental company offering exceptional automobiles for your special day. Whether you’re celebrating in Connecticut, Rhode Island, or Massachusetts, the team at Classic Country Drives can help you find the ideal car for your budget.

Owner Samuel Booth is passionate about the open road and exploration. Having spent more than 18 years developing itineraries for elite clients, he’s well-versed in what it takes to plan the ideal adventure.

You and your partner can give Sam a ring and discuss what you’re looking for, whether it’s transportation for the wedding or a post-ceremony road trip. As for the cars themselves, you’ll be spoiled for choice with options like the Triumph TR6, Fiat 124 Spyder, and MGB Roadster. The team can provide wedding signage to proclaim your love story and even provide you with road books to keep the adventure going. You can book your rental car from 8 AM to 7 PM, with a minimum booking of at least four and a half hours. Talk to the team, though, if you’re looking to take your car overnight somewhere. Needless to say, Classic Country Drives would be delighted for you to drive one of their cars on your special day.

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Frequently asked questions

What types of vehicles are in your fleet?

Classic Car

Schedule permitting, which of the following driving services do you provide?

Round Trip

Typically, what is the minimum rental time required to book your services during peak season?

4+ Hours

Which of the following amenities are your vehicles equipped with?

Wedding Signage

Reviews of Classic Country Drives

R&S
R&S Sent on 06/09/2026
5 out of 5 rating

Thank you, Sam, for a wonderful wedding day experience!

Sam was wonderful to work with. He arrived right on time, had the car beautifully decorated, and was ready to go when we needed him.

After we took some initial photos near the venue entrance, he thoughtfully moved the car to a scenic green space so we could get additional shots with a more natural backdrop. That extra effort made a big difference in the final photos and overall experience.

Everything was seamless from start to finish. He was organized, professional, and made the entire process incredibly easy on an already busy day.

Most of all, Sam was genuinely kind and pleasant to work with, which made the experience even more special. We are so grateful he was part of our wedding day. Love, R&S
We're all about trust. Our community relies on honest reviews to help you make those big decisions with ease.

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