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  • Distance: 41.1 km from Gloucester
    Sat, Aug 01, 2026 at 5:00 AM

    Ride for the Boston Bruins Foundation's Pan Mass Challenge team this summer! The PMC's mission is to raise funds for cancer research and treatment at Dana-Farber Cancer Institute. 100% of every rider-raised dollar goes directly to Dana-Farber. The PMC offers 14 fully supported routes - from 25 to 186 miles - with different levels of cycling ability, fundraising capacity and logistics. As part of the Boston Bruins Foundation's PMC team, you will get special Bruins-themed PMC swag, exclusive fundraising help, bussing to the start line, and the support of our team members throughout the whole PMC weekend. The Pan Mass Challenge 2025 will take place August 1 & 2, 2026.

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    Cycling via RunSignup
  • Distance: 42.4 km from Gloucester
    Sat, Aug 01, 2026 at 8:45 AM

    Every child is a winner in this race! Our goal is to create a fun, relaxed, and inspiring experience for kids ages 6 to 14.

    The race begins at the Cohasset Swim Center, offering easy access with convenient parking nearby. The swim portion takes place in a fantastic 25-yard outdoor pool. The bike and run segments are held on Sohier Road, a two-lane route fully closed to vehicle traffic.

    CATEGORIES:

    • 8 & UNDERS (Swim 2 lengths of the pool, Bike 1.4 miles, Run 1/2 mile)

    • 9-10 YEAR OLDS (Swim 4 lengths of the pool, Bike 1.4 miles, Run 1 mile)

    • 11-12 YEAR OLDS (Swim 6 lengths of the pool, Bike 1.4 miles, Run 1 mile)

    SPACE IS LIMITED T0 250 KIDS

    For all of the details about this race, please go to this page https://www.streamlineevents.com/kids-tri-cohasset

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    KidsRunSwimTriathlon via RunSignup
  • Distance: 27.1 km from Gloucester
    Sat, Aug 08, 2026 at 8:00 AM

    Register for Massachusetts' Premier Bike Ride & Beer Festival 2026! BIKES & BEERS Cycling Event Series is coming to RIVERWALK BREWING for the Best Bike Ride & Beer Event in the business! Ride a 15, 30, or 45-mile route through the beautiful area of Newburyport, Massachusetts followed by a post-ride Beer Festival! Bikes & Beers NEWBURYPORT is the area's premier cycling event departing from RIVERWALK BREWING and traveling the scenic roads of coastal MA. All rides feature morning fuel stations, marked routes, GPS turn-by-turn instruction, rest stops, refreshments, ride marshals, and SAG support. Finish back at RIVERWALK BREWING for a beer festival atmosphere of rewarding craft beers, live music, a charity raffle & much more!

    This is a ride for everyone - All riding levels are welcome!

    WHAT IS BIKES & BEERS:

    • Pick your ride distance and create a team of friends & family (optional)

    • Mark your calendar for a fun day of cycling and craft beer!

    • Pre Ride:

    • Check in a half-hour before your start time

    • We'll provide parking & further ride info in email instructions

    • Enjoy free coffee & fresh pastries

    • Local bike shops offering last-minute tune-ups

    • The Ride:
    • Ride your distance with ride leaders

    • Fully marked routes & GPS turn-by-turn instructions

    • Mechanical support vehicle

    • Rest stops with snacks & refreshments

    • Post Ride:
    • It's time to enjoy (2) complimentary beers on us!

    • Official co-branded Bikes & Beers Pint Glass for every rider

    • Bikes & Beers high-quality neoprene koozies

    • Enjoy the food trucks, live music, games

    • Check out our Bikes & Beers merch tent & snack stand

    • Live raffle with $3,000+ in prizes!

    • Join & Post your photos on our Facebook Page
    • Keep in touch with your newly made cycling friends!

    *Further event information will be communicated in emails after registration and in the days and weeks leading up to event day!

    WHAT YOU'LL GET:

    • Official Bikes & Beers X RIVERWALK BREWING 2026 Pint Glass

    • (2) RIVERWALK BREWING Craft Beers is ON US!

    • High-Quality Neoprene Beer Koozies

    • Raffle Ticket with a Chance to WIN PRIZES!

    • Collectible Bike Plate - Event Photos!

    • Unique Pretzels & Athletic Non-Alcoholic Beer

    • Entry into the Post-Ride Party with LIVE MUSIC, RAFFLE, GAMES, FOOD TRUCKS & MORE!

    FEATURES TO OUR 2026 EVENTS:

    • PROFESSIONAL PHOTOGRAPHERS - At least (3) photographers will be snapping pics of your Bikes & Beers experience during pre-ride, during the ride, and post-ride! We have amazing photo ops!

    • NON-ALCOHOLIC BEER OPTIONS - Still want to ride with us but don't want the alcohol? We now have Athletic Brewing sponsoring all our events! Looks for the blue tent and cooler full of flavorful non-alcoholic brews!

    • COLLECTABLE BIKE PLATES - At check-in, you'll receive a collectible event wristband and bike plate designed just for this event! They look awesome!

    • SPONSOR SNACKS & GIVEAWAYS - Morning coffee, fresh pastries, post-ride pretzel necklaces, recovery protein & much more!

    IT'S A CELEBRATION OF CYCLING AND CRAFT BEER!

    Riders will also receive a free raffle ticket for a chance to win a brand new TUESDAY bike and a ton of other prizes including a private brewery tour and cycling gear!

    Benefitting local cycling charities to help improve the cycling conditions in your area. Have fun, and give back!

    See full details
    15 Miles30 Miles45 MilesCyclingWalk via RunSignup
  • Distance: 25.2 km from Gloucester
    Sat, Aug 15, 2026 at 11:59 PM

    The Blazing Saddles Century, presented annually by the North Shore Cyclists, is a gateway event to the fall schedule of cycling events in New England. The Blazing Saddles Century offers four road routes, each featuring highlights of Boston's North Shore area. Route choices ranging from 36 to 100 miles make the BSC suitable for a wide range of cycling abilities.

    This year's event will also include a 41-mile mixed-terrain route along a variety of rail trails, fire roads, and single track, with 62% overall non-paved surfaces. Five bailouts points are offered to leave the mixed-terrain pathway.

    Ride-with-GPS routes will be shared with registrants closer to the date of the event. SAG/mechanical support will be provided across the routes and at the rest stops.

    Event Schedule for Saturday, August 15th:

    • 7 am - Registration opens

    • 7 to 8 am - 100, 80, and 65 mile and mixed-terrain rides start

    • 8 to 9 am - 36 and 52 mile rides start

    • 11 am to 3:30 pm - Picnic lunch

    FEES:

    • $65 NSC members / $70 non-members, until June 30

    • $75 NSC members / $80 non-member, July 1 - August 11

    • $95 All, August 12-15

    To register at the member rate, NSC members will need to provide the event coupon available on the NSC Blazing Saddles web page after logging in.

    A commemorative Blazing Saddles Century T-shirt will be offered to all participants who register by July 31.

    For additional information, please visit the event website.

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    CyclingTrail via BikeReg
  • Distance: 42.3 km from Gloucester
    Sun, Aug 23, 2026

    Join us this summer for one of the most exciting races of the year. With a one-of-a-kind course that includes beaches, paths, and well-paved closed roads – all in the City of Boston!

    Event details and schedule

    Triathlon via Active.com
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