Rollin Irish Loop - Road Running

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A half-marathon length loop of rolling hills along beautiful back country roads of Vermont. Extremely scenic and fun, but not for the faint of heart.

Written by

Suzanne Loring


13.1 miles

Destination Distance From Downtown

7.7 miles


4 of 5 diamonds

Time To Complete

2 hours

1.5-3 hours


All Seasons

Dog Friendly


Fees Permits




This 13.1 mile road run is a picturesque route on the mostly rural backroads of small-town Vermont. The landscape is dotted by farmland, open fields, forests and panoramic views of the surrounding mountains. It cruises along a mix of paved and dirt roads through the towns of Essex, Milton and Westford. Beginning at the corner of Towers Road and Chapin Road the run proceeds up Chapin for about a mile to Colonel Page Road on the left and after about a mile crosses to Brigham Hill for just under four miles. The loop then takes a right onto Duffy, where runners will be for a very brief time before taking a right onto Rollin Irish for over three miles. At the end of Rollin Irish, runners cross Old Stage Road to Wood Hollow and make an immediate right back onto Chapin for the final four miles. There is an annual race held every April by the Green Mountains Athletic Association along this route.

What Makes It Great

The Rollin Irish Loop is full of variety and you never know what to expect. From gradual and sustained climbs to steep descents and rolling hills the route will give runners quite a workout. The run itself feels like a rollercoaster ride at times with all of its ups and downs, its lowest point coming in at 290 feet after a very steep descent between miles four and five and its highest at 730 feet around mile nine following a rolling but sustained incline. Runners start and finish the race at 485 feet.  

The winding and twisting backroads make coming around the corner a treat with surprise views around every turn. There’s beautiful farmland and old barns, horses and apple orchards, views of the countryside and mountains.

The best part of the run is on its namesake, Rollin Irish itself. Starting out with magnificent views of the Vermont countryside, it continues on into Westford where the road narrows and becomes seemingly much more rural with less houses and more tree-lined sections and farmland. Like the rest of the run, its twists and turns keep runners motivated to see what’s around the next bend. At one point near the end of Rollin Irish, the rolling hills are so close together it feels as though you are running along the back of a sea serpent. This is a great out and back run in and of itself for a total of just over six miles if you are looking for something fun, but shorter.

The last four miles, while still holding true to the route’s reputation for rolling ups and downs, has a trajectory that is more downward than its counterparts, Brigham Hill and Rollin Irish, making it a nice finish to a challenging 13.1.

Who is Going to Love It

Runners looking for a longer run with a good hill workout mixed in will not be disappointed. While the hills are mostly rolling throughout the route, some of the “rolls” are pretty steep, and there are a handful of sustained steeper climbs mixed in that will get the heart pumping. There are plenty of spots to stop for a picture or just grab some water and enjoy the view.Intermediate and beginner runners looking for a shorter, but still scenic and challenging run, will enjoy the out and back on Rollin Irish for a total of six miles.

Directions, Parking, & Regulations

The route starts in Essex at the corners of Towers and Chapin roads. Parking is tricky. Most people park at Memorial Hall, which is at the beginning of Towers Road about a half a mile from the loop's start. If you park here, you add an extra mile onto the route, but it is your safest bet. 

There are no fees for this run and hours are open.

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Rollin Irish Loop

Corner of Towers and Chapin Roads
Essex, VT, 05452
44.517026, -73.066103

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