middlebury greenway

Bike and Brew on the Middlebury Greenway

Trail: Middlebury Greenway

Length: 4.5 miles

Type: Asphalt

Starting Point: 6 Woodside Ave, Woodbury, CT

The Middlebury Greenway is a paved 4.5 mile trail (9 miles round trip) available to bikes, walkers and wheelchairs and extends from Quassy Amusement Park to Straits Turnpike/SR 63 at Woodside Ave in Middlebury, CT. 

As for parking, I suggest parking in Maggie McFly’s parking lot located on 6 Woodside Ave in Middlebury, CT. The trail begins right along Route 63 at the corner of the parking lot on an uphill slope. It touches on several business districts and parks and offers benches along the trail for those who enjoy taking in the scenery. 

Bite + Brews Along the Way
Maggie McFly’s would be my first suggestion, which is a local craft eatery and bar. They showcase many local CT vendors such as locally sourced beef, sausage, cheeses, cupcakes, craft beers, spirits, wine, and more.

Pies & Pub is another option located on 1 Store Rd in Middlebury is approx. a halfway point on the trail (if traveling one way). It was originally known as Pies and Pints and offers pizza, wings and burgers along with a decent craft beer list on tap.

What I liked most about this trail

As a bike rider I found it to be challenging uphill one way and then downhill on the way back. It was the perfect combination for a short bike ride, which ended with some great local craft beer and food.