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Driving Time between Brookline, Massachusetts and Winchester, Massachusetts

  • Halfway Point
  • Points of Interest
  • Travel Time
  • Travel Cost
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Exploring the Best Routes from Brookline to Winchester

In search of a quick getaway from Brookline? Winchester is a perfect choice. This lovely Massachusetts town is filled with activities to make your visit a memorable one. The best part? The drive from Brookline to Winchester is pretty straightforward, and depending on the route you take, it can be as short as 20 minutes. To help you plan your journey, we've compiled a list of routes to Winchester, where you’ll discover the distance and drive duration.

The Quickest Route

When it comes to driving from Brookline to Winchester, first things first: you need to know the fastest route. Take the I-93 N, and you’ll cover a distance of around 11 miles, which will take approximately 20 minutes by car in light traffic. While this is certainly the quickest option, it might be a bit congested during rush hours, so keep that in mind while planning your trip. Along the way, you can make a stop at the Middlesex Fells Reservation to stretch your legs or one of the numerous diners and coffee shops in Stoneham, Massachusetts.

The Scenic Route

This route might not be the fastest, but it’s hands down the most scenic drive from Brookline to Winchester. You’ll cover approximately 14 miles by taking Route 2 W and Route 3 N. It will take approximately 45 minutes to complete the journey but promises picturesque views of Massachusetts countryside. You can take a break and stretch your legs at Lexington Battle Green, and make sure to grab a bite at one of the charming eateries in Lexington, Massachusetts.

The Historic Route

If you're someone who loves history, then this route is for you. Take I-90 E towards Cambridge, Massachusetts, to get on MA-2A E. You’ll cover a distance of around 16 miles, which will take approximately 35 minutes. Along the way, you'll find yourself in the heart of historic Cambridge, home to Harvard University, MIT & numerous landmarks. Take a stop by the Henry Wadsworth Longfellow House or the Paul Revere House. Grab a coffee and a famous Boston Cream Pie at Flour Bakery + Café.

The Off-The-Beaten-Path Route

Looking for an alternate route filled with quirky landmarks? Take MA-28 N and MA-60 W, and cover approximately 12 miles, which will take approximately 30 minutes. This route may not be the most time-efficient, but you'll see amazing sights such as the Necronomicon Tribute in Medford, Massachusetts, and the oldest candy store in the US, Ye Olde Pepper Companie in Salem.

Whichever route you choose, you're sure to have an amazing time exploring Winchester, Massachusetts. Enjoy the ride!

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