The Great River Ride is back for 2026!
Presented by the Friends of the Columbia Greenway Rail Trail and New Horizons Bikes, the Great River Ride brings you an amazing set of rides in the Westfield River watershed. Soak in the sights along the beautiful Westfield River as you ride through stunning autumn foliage.
See details for each type of ride below. All routes start and end at Sons of Erin, where a buffet and live entertainment will be waiting for you at the finish!
At-a-glance
| Route | Distance | Terrain & Surface | Key Highlights | Best Suited For |
|---|---|---|---|---|
| Vineyard Trail Route | 28 Miles | 100% Paved Rail Trail (Flat) | Brignole Vineyards, Hot Baked Potato Stop & Wine | Families, casual riders, & E-bikes |
| Vineyard Road Route | 40 Miles | Paved Rail Trail + Rolling Roads | Brignole Vineyards & Scenic Country Roads | Intermediate riders wanting a bridge to road riding |
| Metric Century | 65 Miles | Paved Hilltown Roads (Challenging) | Fall foliage, rushing waterfalls & scenic climbs | Conditioning road cyclists & club riders |
| Century Route | 85 / 103 Miles | Paved Hilltown Roads (Epic) | Historic Keystone Arches, Wild & Scenic River | Experienced century & endurance road riders |
| Gravel Route | 72 Miles | 40% Dirt/Gravel, 60% Paved | Knightville Basin, Chesterfield Gorge, Gated Woods | Adventure & gravel riders (38mm+ tires required) |
Vineyard routes
The 28-mile Vineyard Route follows the smooth, scenic paths of the Columbia Greenway Rail Trail, Southwick Rail Trail, and Farmington Canal Heritage Trail—all part of the historic New Haven & Northampton Canal Greenway. You’ll ride south across the state line to Brignole Vineyards in East Granby, CT, where you can refuel at our featured rest stop with our famous hot baked potato and tasty snacks (with wine available for purchase!) before heading back to Westfield.
This flat, trail-based ride is ideal for cyclists of all experience levels and families looking to enjoy our premier rail trail network. Pedal-assist e-bikes are warmly welcome, and kids 15 and under ride free with a registered adult!
Looking for a little extra distance? The 40-mile Vineyard Route combines these scenic rail trails with rolling open roads for the perfect balance of trail cruising and on-road challenge—complete with that same relaxing stop at Brignole Vineyards.
Road routes
Get ready for knee-popping climbs, breathtaking vistas, fast descents, and peak autumn foliage as you tour the historic hilltowns of the Eastern Berkshires. Along the way, you'll roll past miles of classic New England stone walls, rushing waterfalls, iconic white-steeple churches, colonial homes, historic keystone arches, and a designated Wild & Scenic river—and yes, plenty more hills!
Best of all, you'll stay fueled with rider-staffed rest stops packed with snacks and local hospitality, including our famous "Baked Potato" stop.
Choose between 103-mile, 85-mile, and 65-mile options.
Gravel route
The Gravel Route is a classic mix of pavement, gravel, dirt, and seasonal roads that we’ve enjoyed riding every autumn for over 50 years.
Spanning 72 miles (40% unpaved), the route takes you deep into the remote Knightville Basin and Chesterfield Gorge, offering stunning vistas along the East Branch of the Westfield River. Along the way, you’ll roll past Knightville Meadows, Rainbow Pool, Little Gorge, and Chesterfield Gorge.
While most climbs are paved, Thayer Rd. delivers a punchy 1.4-mile dirt ascent with grades ranging from 7% to 10%. A long descent down a seasonal road leads toward River Rd., featuring a few steep, thrilling downgrades. At River Rd., you can choose your own adventure: tackle the final gravel climb up Maynard Rd. or take the paved bailout route up East River Hill straight to the Chester Hill Church, where you will find our famous "Baked Potato" stop.
Rider Notes & Safety
Support & Connectivity: Gravel and dirt sections are unsupported by SAG vehicles, and cell service is limited. Be prepared to handle your own flats and mechanicals.
Vehicle-Free Miles: Several miles follow a gated road closed to motor traffic—an ideal spot to team up and ride with a group.
Equipment: Tire widths of 38mm or wider are strongly recommended.
Autumn Conditions: Fallen foliage can obscure loose gravel and bony surfaces; exercise caution on all descents.
Event Details & Rider FAQs
Start Location & Parking: All rides start and finish at the Sons of Erin (22 William Street, Westfield, MA). Free on-site and nearby event parking is available.
Start Time:
6:00 AM: 200K Brevet (RUSA)
7:00 AM: 100-Mile Century
8:30 AM: 72-Mile Gravel Route; 85-Mile & 62-Mile Metric Century
11:00 AM: 40-Mile & 28-Mile Vineyard Routes
(Please stick to start times so rest stops and volunteer staff are open and ready for you!)
What’s Included with Registration:
Fully stocked rest stops featuring snacks, hydration, and our famous hot baked potato stop (at Chester Hill Church and Brignole Vineyards).
Post-ride hot buffet and live entertainment at Sons of Erin.
Marked courses, digital GPS routes (RideWithGPS), and printed cue sheets.
SAG vehicle roaming support on paved road routes.
Navigation & GPS Files: Updated RideWithGPS links and printable cue sheets will be emailed to all registered riders prior to the event and available at morning check-in.
Support & SAG Coverage: Roaming SAG vehicles provide mechanical and transport assistance across the paved road routes. Please note: Gravel and remote dirt sections are unsupported by SAG vehicles—gravel riders should carry extra tubes, a pump/CO2, and basic tools.
Weather & Gear: This is a rain-or-shine event (no refunds). Fall mornings in New England can start crisp and foggy—we recommend layering, bringing a spare tube and inflation tool, and equipping headlights/taillights for early morning starts.