Middlesex Driving Academy

At Middlesex Driving Academy, driving is more than just a skill—it's an empowering journey. Nestled in the welcoming city of Winchester on Swanton Street, this owner-operated school dives deep into the nuances of road safety and driving confidence.

Here, students find not only comprehensive driver education classes, but also specialized behind-the-wheel training. Whether it’s sharpening skills with experienced instructors or understanding local driving rules from another perspective, every lesson is designed to enhance readiness for both novice and seasoned drivers alike.

Operating daily from 10:30 AM to 7:30 PM, this academy prides itself on accommodating busy schedules with flexible lesson times. Their dedication shines through in their personalized approach: small class sizes ensure ample attention while on-site road tests keep worries at bay.

Calling connects prospective drivers to a supportive team eager to answer questions or set up appointments. With multiple success stories under its belt, the driving school stands resolutely committed to helping individuals conquer their driving fears and master the road—all while creating unforgettable memories along the way.

Contact

Hours

Monday10:30 am - 07:30 pm 
Tuesday10:30 am - 07:30 pmOpen now
Wednesday10:30 am - 07:30 pm 
Thursday10:30 am - 07:30 pm 
Friday10:30 am - 07:30 pm 
Saturday10:30 am - 07:30 pm 
Sunday10:30 am - 07:30 pm 

Map

FAQ

What is the phone number of Middlesex Driving Academy?

The contact phone number is .

What is the address?

Middlesex Driving Academy is located at 66 Swanton St, 01890 Winchester, Massachusetts. Find out .

What are the opening hours?

The school's opening hours for today, Tuesday, are from 10:30 am to 07:30 pm, so it's open right now. Check the schedule for more information.

Open on weekends?

Yes, Middlesex Driving Academy is open on Saturdays and Sundays from 10:30 am to 07:30 pm.

Do the students recommend it?

This driving school has got a positive average rating of 4.48 out of 5 based on over 140 reviews on Facebook, GetPassed and Google. Below you can see the most relevant ones.

Reviews

Dave L.
5

Im in my early 40s, grew up in NYC, lived in Boston and just never ended up getting a license. Once my wife and I bought a house in Medford it was time. There wasnt a not nice person there, supportive and great. I especially have to call out Joanie (Ms Fiore) cause she was 85% of my lessons. Perfect amount of calming sass, yet also assistance when you have questions and never caused stress. I passed my road test on first try. This place is 100% encouraged for people of all ages. Theres no convenient...
way to do it on either side, but I do wish they could lock the same instructor for each lesson. Theyre all good, but some teach differently than others, and if you get someone that isnt your usual it causes unnecessary nerves if their style is not the same.

Thomas M.
5

Middlesex Driving Academy is the best. Always helpful when you don t understand the process, kind people, and effective instruction. I got my license on my exact day of eligibility. Instructors really take an interest in their students capabilities and well being. Thank you Middlesex.

Jenny V.
5

An amazing driving school! I enjoyed my time learning with Mrs. Ryan! She truly makes driving for a new learner a great experience! The whole staff at MDA are extremely friendly and cooperative! Mr. Smith is hilarious! I am forever grateful and thank you to the teachers for the time you take to teach us students! - Jenny with HER LICENSE

Krushna R.
5

I am here in MA on a visa with some driving experience in India. Wanted to get acquainted with the rules here so took the driving lessons with the school and passed the road test on the second attempt. The school is very well organized and usually busy with many students but they helped me get the sessions in the evening time so that i didnt had to miss my office hours. They are lovely people and the owner has a very good sense of humor :). Overall I am very delighted with the experience.

Enakshi C.
5

Such a lovely vibe of this school. I did learn driving from a different school but they didn t know the tips that you need to know during the test and I failed. But then I heard about Middlesex and after hearing my story, Mrs Ryan was great by taking me on a test drive and helped me with the rules and tips I needed to follow during the test. Mr Smith too helped with his suggestions and best practices to follow while on road. I did pass my test and kudos to them.

Arianne M.
5

Highly recommended! The whole staff is very supportive and excellent instructors. I have llittle to no experience in driving at all. I took a 6hr driving lessons and passed the road test. I am most thankful to Mr. Smith! He is a wonderful instructor, very detailed, and supportive.

Ryan M.
5

Just passed my road test here today after taking the 6 Adult Lessons package! Before coming to this school I was terrified of driving. They helped me through that, and helped me feel (reasonably) comfortable and eager to keep practicing! The owner, Rick, has been very reassuring and friendly from the start. I had the pleasure of learning from Mrs. Fiore and Mrs. Ryan, who I had an excellent experience with! I would definitely recommend this school both to student or adult learners!

Tammie P.
5

Our family loves this driving school! We just had our 4th and last child to complete the program and passed his road test yesterday! They are professional, friendly and full of information! The instructors are amazing! All four of my kids were incredibly prepared for their road test. Also, the convenience of taking the road test at the driving school and not having to go to the registry is immeasurable! They take the stress out of everything! Thanks Mr. Smith!

Eduarda S. R.
5

Very good driving school! I did all my lessons and a road test there and everything went good ! I passed first try road test. I definitely recommend ,they are very flexible with lessons and are try to best to be fair with everyone.

Wasei L.
5

The entire staff was incredibly supportive and patient throughout the entire process. No matter how many times I emailed or called asking questions, Ricky, Amanda, and others explained things clearly and calmly, and never made me feel discouraged. Their support really boosted our daughters confidence behind the wheel. Thanks to their excellent instruction and unwavering patience, she passed her driving test! I highly recommend this driving school to anyone looking to learn how to drive in a supportive and positive environment.

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