local tours


beginner to advanced

* Covi-19 update May 2020.  Frontier is taking the coronavirus and touring seriously.  I want your visit to Western Massachusetts and tour with us to be one that is enjoyable and safe.  While we do have a relative low number of cases in this area, it is still not advisable to travel for tourism at this point.  The riding is great here and will be for a long time to come.  Send me an email or give me a call to let me know when you might be in the area so we can arrange for safe and enjoyable tour.  Now, read on…

Find out what awaits over the next hill and feel like a kid again!

Frontier Cycling crafts fun and exciting cycling tours in The Pioneer Valley and Western Massachusetts.  I am excited to show you why I chose to start Frontier Cycling Tours! Together we can explore the crunchy gravel back roads and windy by-ways of the Pioneer Valley and Western Massachusetts hill towns, stopping for a locally roasted coffee or cold craft beer along the way at one of the many family run businesses. So, grab some friends or come alone there is so much to experience on a bike, from challenging climbs, cool descents and leisurely meanders, there is truly something for everyone.

Frontier Cycling offers a diverse range of routes and rides to choose from. All rides are customizable according to the experience you wish to have and can be added onto. The following suggested rides are considered Half-day rides finishing in 4 hours or less depending on skill and fitness levels.

Prices are as follows:

  • $250 for 1-2 riders
  • $400 for 3-4 riders
  • $600 for 5-6 riders

No cancellations less than 24 hours in advance

Let’s discuss a tour!


Ashfield-Hawley Loop

Ashfield Hawley ride

Part of the Massochista bike race, this hilly 30 mile loop starts in the quaint town of Ashfield and climbs up to Hawley, winding its way through forested gravel paths and carless backroads into Ashfield, with a swim in the local pond.

The Valley Meander

This relatively flat 25 mile ride starts in the Historic Deerfield center, crosses the Deerfield River then traverses farm fields as we follow the rivers path as we cross over into South Deerfield and back into Historic Deerfield again.. This ride includes a stop at the Montague Bookmill, where you’ll find “all the books you don’t need in a place you can’t find”. A nice optional climb up to North Leverett will work your legs just a bit more.

The Brewery Tour

If you like beer ( I do!), grab some friends and we’ll create the perfect path to taste several local brews. There are long and short options available as there are several breweries within rideable distances. My favorites are Element Brewing, Floodwater Brewing, Hitchcock, and Berkshire Brewing Company. In between, you’ll see some of the regions most beautiful landscapes.

Conway to The High Ledges

Shelburne ride

One of my favorites! This roughly 26 mile ride starts in the town of Conway, one of our many former mill towns. We wind our way through the backroads into Shelburne Falls, where we can experience the famous Bridge of Flowers. The last segment is a hilly climb to the High Ledges, which offers a stunning panorama of the Deerfield Valley.

Sunderland to Brattleboro

Currently we also offer one full-day group ride from Sunderland to Brattleboro Vermont. Over the course of 60 miles, you’ll see and experience the Connecticut River Valley in a very personal way. Pass by a Hop farm growing hops for the numerous craft breweries, fertile farm fields growing organic produce and small towns as we ride along the Connecticut River. After a nice ride and lunch in Brattleboro, a van will bring us back home where you can enjoy the rest of your evening as you wish. This ride must be reserved two weeks in advance for planning and logistics.

If you and your friends have something else in mind, let me know what it is. I’ll do my best to make sure your experience with me is memorable and rewarding.

All rides include a coffee/beer break, snack, company T-shirt and water bottle.


reach out and let’s start planning

Contact Us