Century Rides in Massachusetts
The comprehensive 2026 directory of 100-mile centuries, metric centuries (62 miles), and endurance cycling tours across Massachusetts.
Cycling in Massachusetts: Terrain & Route Overview
Massachusetts is steeped in cycling history and offers some of the most scenic and diverse century routes in the Northeast. In the west, the Berkshire Mountains deliver demanding alpine climbs, shaded river gorges, and rewarding panoramic summits. Across central Massachusetts, century routes wind past historic Revolutionary War battlegrounds, colonial stone fences, and tranquil apple orchards. Along the coast, riders can experience the flat, ocean-scented roads of Cape Cod, Martha's Vineyard, and the North Shore. Events like the Pan-Mass Challenge highlight the state's passionate cycling community and unmatched fundraising dedication. With excellent shoulder seasons, vibrant fall foliage, and superb cycling infrastructure, Massachusetts is an extraordinary state for 100-mile exploration.
Terrain Characteristics: Cape Cod seaside dunes, historic colonial woodlands, and steep Berkshire mountain passes.
Riding Season & Weather: May through October.
📍 Massachusetts Century Rides Map
11 Plotted EventsApple Country Century
📅 Aug 29, 2026100 miles of beautiful tranquil back roads that epitomize the bucolic beauty found along some of the most popular bicycle routes west of Boston.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi)🗺️ RWGPS Map |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Aug 29, 2026 |
| RWGPS Telemetry | Interactive Route Map (1) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| Starting Venue | Lincoln-Sudbury Regional High School |
| Street Address | 390 Lincoln St. |
| Location | Lincoln-Sudbury Regional High School, 390 Lincoln St., Sudbury, MA, MA MA |
| GPS Coordinates | 42.383655, -71.428159 (Google Maps ↗) |
| Organizer | NVP ↗ |
| Entry Fee | $50.00 (NVP members), 70.00 (non-members) |
| Registration | Direct Registration Link ↗ |
Bike MS: Cape Cod Getaway
📅 Jun 27 – 28, 2026Take in the beautiful views as you ride from Quincy to Provincetown, MA on this two-day cycling experience with multiple route options from 40 to 100 miles with support every mile of the way.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Jun 27 – 28, 2026 |
| End Date | 2026-06-28T00:00:00 |
| Starting Venue | Mass Maritime Academy |
| Street Address | 1776 Heritage Drive |
| Location | Quincy, MA, MA |
| GPS Coordinates | 42.357603, -71.068432 (Google Maps ↗) |
| Organizer | National MS Society ↗ |
| Entry Fee | Fundraising Minimum: $500 |
| Registration | Direct Registration Link ↗ |
Climb to the Clouds
📅 Aug 16, 2026Climb to the Clouds will test your biking abilities with lots of climbing and a climb up Mt. Wachusett.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi)🗺️ RWGPS Map |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Aug 16, 2026 |
| RWGPS Telemetry | Interactive Route Map (1) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| Starting Venue | Mt. Wachusett Start Hub |
| Location | Massachusetts, MA |
| GPS Coordinates | 42.4867, -71.8897 (Google Maps ↗) |
| Organizer | Charles River Wheelers ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
CRW Cranberry Century
📅 Oct 18, 2026The Cranberry Century is a fall classic in Plymouth MA with beautiful routes passing cranberry bogs to Mattapoisett and back. Come join us for another fully-supported event with 4 beautiful rides, 100 miles, 62 miles and 53 miles and new 35 mile route.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi)⚡ Half Century (50 mi)🗺️ RWGPS Map (3) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Oct 18, 2026 |
| RWGPS Telemetry | Interactive Route Map (3) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| Starting Venue | Myles Standish State Park |
| Street Address | 10 Lower College Pond Rd |
| Location | Myles Standish State Park in Plymouth, MA 02360 |
| GPS Coordinates | 41.910404, -70.642004 (Google Maps ↗) |
| Organizer | Charles River Wheelers ↗ |
| Entry Fee | $Non-Refundable |
| Registration | Direct Registration Link ↗ |
D2R2 (Deerfield Dirt Road Randonnée)
📅 Aug 28, 2026The Deerfield Dirt Road Randonnee is a community campout and celebration with incredible food, drink, and music, offering an exhilarating ride and a unique connection with the natural splendor of our region.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Aug 28, 2026 |
| Starting Venue | Franklin County Start Hub |
| Location | Franklin County, Massachusetts, MA |
| GPS Coordinates | 42.09347, -71.405786 (Google Maps ↗) |
| Organizer | Franklin Land Trust ↗ |
| Organizer Contact | [email protected] |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
North to New Hampshire
📅 May 31, 2026First chance of the year to put in big mileage Did your winter training prepare you to take on this scenic ride up into some of New Hampshire's quiet roads, bringing you along the riverbanks and back to Massachusetts?
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi)🗺️ RWGPS Map |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 May 31, 2026 |
| RWGPS Telemetry | Interactive Route Map (1) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| Starting Venue | New Hampshire Start Hub |
| Location | New Hampshire, MA |
| GPS Coordinates | 42.407211, -71.382437 (Google Maps ↗) |
| Organizer | Charles River Wheelers ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
Pan-Mass Challenge (PMC)
📅 Aug 07 – 08, 2027The Pan-Mass Challenge is a Massachusetts-based bike-a-thon that raises more money for charity than any other single athletic fundraising event in the country. Always held the first weekend in August, the PMC raises funds for Dana-Farber Cancer Institute, a world leader in adult and pediatric cancer treatment and research.
⚡ Event Details & Specifications ›
| Dataset Population | 2027 Forward Calendar |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Aug 07 – 08, 2027 |
| End Date | 2027-08-08T00:00:00 |
| Starting Venue | Hart Center at the Luth Athletic Complex Main Gym at Holy Cross |
| Location | Massachusetts, MA |
| GPS Coordinates | 42.2621, -71.8034 (Google Maps ↗) |
| Organizer | Pan-Mass Challenge ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
| Event Media | View Image / Banner ↗ |
Richard's Ride v66
📅 Nov 07, 2026The old hot rod is getting a year older. To celebrate that event I'm hosting a free ride from the Upper Bend Cafe in Turner's Falls, Massachusetts. There will be three routes but we'll all roll out together. The shorter routes will have hang outs scheduled. The Montague Book Mill will be stop one. From there the long haul truckers push west across the Connecticut River and into the hill towns. After an 11 mile...
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | ⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Nov 07, 2026 |
| Street Address | 112 Avenue A |
| Location | Montague, MA 01376 |
| GPS Coordinates | 42.608002, -72.557315 (Google Maps ↗) |
| Organizer | Domestique Events ↗ |
| Registration | Direct Registration Link ↗ |
Ride to End ALZ New England
📅 Jun 05, 2027Ride to End ALZ New England is a cycling event to support the fight against Alzheimer's disease.
⚡ Event Details & Specifications ›
| Dataset Population | 2027 Forward Calendar |
| Qualified Distances | 🏔️ Imperial Century (100 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Jun 05, 2027 |
| Location | New England, MA |
| Organizer | Alzheimer's Association ↗ |
The Flattest Century in the East
📅 Sep 13, 2026 (7:00 AM – 5:00 PM)This is a NBW member-only event - pre-registration required - Commemorative t-shirt - 39-, 60-, 78- and 100-mile course options - Full ride and rest stop support - Post-ride food, drink, and everything the beach has to offer.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi)🗺️ RWGPS Map |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Sep 13, 2026 (7:00 AM – 5:00 PM) |
| RWGPS Telemetry | Interactive Route Map (1) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| End Date | 2026-09-13T17:00:00 |
| Starting Venue | Horseneck Beach State Reservation |
| Location | Horseneck Beach State Reservation, Westport, MA |
| GPS Coordinates | 44.6789, -76.3982 (Google Maps ↗) |
| Organizer | Narragansett Bay Wheelmen ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
| Event Media | View Image / Banner ↗ |
Watershed Ride
📅 Oct 03, 2027Ride through breathtaking coastal scenes, cranberry bogs, farms, streams and forests
⚡ Event Details & Specifications ›
| Dataset Population | 2027 Forward Calendar |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Oct 03, 2027 |
| Starting Venue | Woods Hole |
| Location | Little Compton, Mattapoisett, Bourne, MA |
| GPS Coordinates | 41.4645, -71.1967 (Google Maps ↗) |
| Organizer | Buzzards Bay Coalition ↗ |
| Organizer Contact | [email protected] |
| Entry Fee | $75 registration fee ($85 after Labor Day) / $300 fundraising minimum |
| Registration | Direct Registration Link ↗ |
| Event Media | View Image / Banner ↗ |