10 running and cycling events in Plymouth, Massachusetts
From big races to Saturday morning group runs—find running and cycling events and connect with the local endurance sports community.
Plymouth
10 events in Plymouth-
Sun, Feb 15, 2026 at 9:30 AMSee full details
PLEASE NOTE THE RACE HAS IS BEING HELD ON:
SUNDAY, FEBRUARY 15th, 2026
@
MAYFLOWER BREWING COMPANY
12 RESNIK RD., PLYMOUTH, MA., 02360
READY TO CELEBRATE CONQUERING THE COLD? THE WINTER WARRIOR 5K IS YOUR CHANCE TO PROVE THAT YOU OUTRAN THE CHILL OF WINTER. THIS ISN'T JUST A RACE, IT'S A CELEBRATION OF THE GRITTY, INVIGORATING CHALLENGE SET AGAINST THE CRISP BACKDROP OF MID-WINTER WHERE YOUR INNER STRENGTH IS PUT TO THE TEST AGAINST THE ELEMENT!
ALL PARTICIPANTS WILL RECEIVE A LONG SLEEVE ASICS TECH SHIRT, A DRINK TICKET TO MAYFLOWER BREWING COMPANY (21+ YEARS OLD; NON-ALCOHOLIC BEVERAGES ALSO AVAILABLE) AND A BRIGHT, SHINY FINISHER MEDAL!
POST RACE PARTY AT MAYFLOWER BREWING COMPANY
Kids run: 9:15am
5K: 9:30am
WINTER WARRIOR 5K
PRESENTED BY:
ASICS
POWERED BY:
MARATHON SPORTS
SPONSORED BY:
MAYFLOWER BREWING COMPANY
Race Details
SUNDAY, FEBRUARY 15th, 2026
KID'S RUN: 9:15AM
5K: 9:30AM
POST RACE PARTY:
Once you finish the race you can grab some water and light snacks (gotta stay hydrated) and then make your inside Mayflower Brewing for your post race celebration, drinks and awards!
BIB PICKUP/ On-site registration (AVAILABLE ONLINE ONLY)
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FRIDAY, FEBRUARY 13th FROM 4PM-7PM AT MARATHON SPORTS (9 COURT STREET, PLYMOUTH, MA., 02360) WITH 20% OFF PURCHASES.
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SATURDAY, FEBRUARY 14th, FROM 12PM-6PM AT MARATHON SPORTS (9 COURT STREET, PLYMOUTH, MA., 02360) WITH 20% OFF PURCHASES.
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SUNDAY, FEBRUARY 15th, 8AM-9:25AM, MAYFLOWER BREWING, 12 RESNIK RD., PLYMOUTH, MA., 02360
WALKERS WELCOME:
Running strollers please start in the back
SHIRT DEADLINE:
All participants will receive a shirt.
AWARDS:
1st, 2nd and 3rd Overall Male, Female & Non-Binary ($25 gift cards to Marathon Sports)
- Age group winner: 10 & under, 11-15, 16-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+ ($25 gift cards to Marathon Sports)
PARKING:
WATER:
Please note we will NOT have a water stop on the course. If you would like to have water while you are running please be sure to bring a bottle or hydration pack. Water will be available prior to the start and will be available at the finish line.
POST RACE PARTY:
Once you finish the race you can grab some water and light snacks first (gotta stay hydrated) and then make your way to Mayflower Brewing for your post race celebration, drinks and awards!
FAQs
What is included in my registration?
In addition to a drink ticket you’ll receive a long sleeve tech shirt and sparkly finisher medal. Some of you early registrants will have a bib with your name on it!
Is the Winter Warrior 5K open to all ages?
Yes! We have no age restriction on registration. If your young ones are comfortable with the 3.1 miles, sign them up to run along with you or they can participate in the ¼ mile “Mini Yeti Run”.
Can I transfer my race number to another person?
Yes! You can transfer your bib to another person up until packet pick-up hours are over. Simply reach out to our Race Director- Becky MacBride ([email protected]) or the Assistant TO THE Race Director- Steve Infa ([email protected]).
Can I run with a stroller?
Yes! We are happy to have you & your little one join us on the race course, but in the interest of safety for all participants, including your child, you will be asked to line up at the back.
Are headphones permitted?
You may wear headphones. We ask that you keep the volume at a reasonable level for your own safety and out of courtesy for fellow participants.
Is there a course time limit?
Yes. Our time limits are set to ensure runners are protected from traffic and have the support they need to finish. The 5K has a one-hour + fifteen minute time limit. Athletes of all abilities are invited to participate, provided they can finish the course within the time frame.
Can I change the size of the shirt I ordered?
Yes, however this must be done AFTER the race and only if there are shirts leftover.
How do I get my bib and swag?
You must attend bib pickup during the time frames and location communicated in the bib number email you will receive on the Monday of race week. Bib pickup will be available at the times listed below:
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FRIDAY, FEBRUARY 13th FROM 4PM-7PM AT MARATHON SPORTS (9 COURT STREET, PLYMOUTH, MA., 02360) WITH 20% OFF PURCHASES.
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SATURDAY, FEBRUARY 14th, FROM 12PM-6PM AT MARATHON SPORTS (9 COURT STREET, PLYMOUTH, MA., 02360) WITH 20% OFF PURCHASES.
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SUNDAY, FEBRUARY 15th, 8AM-9:25AM, MAYFLOWER BREWING, 12 RESNIK RD., PLYMOUTH, MA., 02360
Can someone pick up my bib for me?
Yes. They will need to know your bib number.
Can you mail my race swag?
All race items must be picked up during bib pick-up hours before the race. Swag will ONLY be mailed to those who registered to run with us virtually.
Where can I find results?
Results will be posted here!
Will there be portable toilets available?
Portable toilets will be available in the starting area of the race throughout the event.
What is your bad weather policy?
It is our goal to ensure a safe event for all involved. We will not expose participants or the community to undue risk as a result of staging the event. The 5K will take place rain or shine. However, when weather or other physical conditions present a danger to participants, we maintain the right to cancel the race. Less threatening conditions could result in an alteration of the course or race length to ensure safety for all. We highly recommend you purchase the race insurance at checkout.
Do you allow refunds?
All entries are final. There will be no refunds or deferrals.
How do I volunteer?
Volunteer's should reach out to our Race Director: [email protected]
Where should I park on race day?
TBD
Is there a water stop along the route?
We will NOT have a water stop on the course. If you would like to have additional water while you are running please be sure to bring a bottle or hydration pack. Water will be available prior to the start and will be available at the finish line.
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Sat, Jul 04, 2026 at 7:30 AMSee full details
Kick off your 4th of July holiday with the 11th Annual 4th of July 5K. Get in a morning run and finish by the annual 4th of July parade reviewing stand. The best way to access premium spots for parade viewing.
Adult (18+)
$30.00 through May 31st
$32.50 June 1st through 28th
$35.00 June 29th through July 4th
Student (11-17)
$25.00 through June 28th
$27.50 June 1st through 28th
$30.00 June 29th through July 4th
Child (10 & under) and Senior (70+)
$20.00 through June 28th
$22.50 June 1st through 28th
$25.00 June 29th through July4th
Select the NO SHIRT option when you register to receive a $10 registration discount (discount available through the shirt deadline of June 14th).
On the morning of July 4th bib pickup and on site registration will take place from 6:30 am - 7:15 am at DCR Pilgrim Memorial State Park on Water Street.
All race registration is online only. We will not be offering paper registration forms at pre-race pickup or on race day.
AWARDS
Overall 1st, 2nd and 3rd Male and Female
1st, 2nd and 3rd male and female in the following age groups:
10 & under, 11-15, 16-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+
Parade information can be found at: https://july4plymouth.com/
RUNNER SAFETY:
No dogs allowed on the course. If you need to participate with a trained service animal please send an email to [email protected].
SHIRT DEADLINE: Sunday, June 14th @ 11:59pm EST
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Sun, Aug 09, 2026 at 7:00 AMSee full details
The Cycle Against Suicide Pilgrim Tour is a fundraiser for Cycle Against Suicide. You entry fee includes a one way ticket on the Fast Ferry from Provincetown to Plymouth, SAG and luggage service, marked route, GPS route, ride jersey and a donation to Cycle Against Suicide. We encourage fundraising through Pledge Reg. Every donation makes a difference
Cycle Against Suicide is charity that makes a valuable contribution to the public education of mental health by changing the narrative surrounding suicide. When an individual is vulnerable enough to consider taking their own life, silence is read as indifference. With hundreds of people dying by suicide each year and research indicating that thousands more contemplate it, we all have a role to play to collectively address the challenges that suicide presents. In a bid to save more lives, Cycle Against Suicide through its programmes, sets out to change culture and create a society that openly talks about suicide to allow people to speak up and seek help.
It’s OK not to feel OK; and it is absolutely OK to ask for help’
More Helpful Information
Rules of the Road Ride
This is a rules of the road ride, not a race. You must obey traffic lights, stop signs, ride no more than two abreast when safe to do so. The route uses the Cape Cod Rail Trail. Use caution as the trail is very busy on Sundays. Please walk over the Sagamore Bridge
Start
The start is at Jenny Pond, Spring St, Plymouth. There is free parking at the start area. Additional free parking is available on Water St here which is about one mile from the start and about one half mile from the Fast Ferry https://maps.app.goo.gl/9xqAH9SuDdPQAhTt8. There are a few spaces here as well https://maps.app.goo.gl/o7qLKqjTwgqDoTDX9
Route
Scan here to download the ride route from Ride With GPS
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Or here on Garmin Connect
https://connect.garmin.com/modern/course/310400243
There is SAG support on the route and the SAG willbe at three locations on the route. There will be a bike tech at the start and at the 62 mile mark.
Provincetown
The finish is at Herring Cove Beach. There are showers available. Provincetown Center is two miles away and there are plenty of places for dining and having an adult beverage.
Fast Ferry
The Fast Ferry leaves at 4:15pm from MacMillan Pier. Don't miss it or you will have a long bike ride or UBER ride back to Plymouth. The Fast Ferry docks at the State Pier on Water St when returning.
Lodging Information
There are numerous lodging option in Plymouth, hotels, motels, inns, B&B's, you name it. See Plymouth is a great resource for finding lodging. A good place to start is https://seeplymouth.com/listings/lodging . They can be very helpful if you have a group call 508 927 6607
Lodging nearby:
Governor Carver Inn, 25 Summer St. Directly across from the start area. 508 595 4033
The Hilton Garden Inn, 4 Home Depot Dr, 2 miles by bike or car to the start area 508 444 5775
Hotel 1620, 180 Water St, 1 mile by bike or car to the start 508 747 4900
Cold Spring Best Western, 180 Court St, 1 mile by bike or car to the start area 508 746 2222
Bike rentals
Corner Cycle, Falmouth 508 540 4195 - please mention Cycle Against Suicide
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Sun, Oct 18, 2026 at 7:00 AMSee full details
CRW Cranberry Century - Oct 18, 2026
The 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. The CHC captures some of the most charming roads in New England. It is also relatively flat and very manageable for riders of all abilities. All rides start at Myles Standish State Park in Plymouth and travel through the cranberry bogs in Rochester, Wareham, Carver, and Acushnet. Rides include rest stops at Eastover, Tamarak and on the beautiful wharf in Mattapoisett. You will enjoy food and drink at rest stops along the route and after party at College Pond at the finish.
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Sun, Oct 18, 2026 at 9:30 AMSee full details
Run for Donuts (and Beer!)
at Plimoth's Cider Donut 5K!
Get ready to earn your treats at Plimoth's 2nd annual running of the Cider Donut 5K on Sunday, October 18th, 2026 (starting at 9:30am)! This deliciously fun 5K run or walk promises a fantastic autumn morning for all ages and fitness levels.
Lace up your sneakers and hit the scenic course, knowing that a well-deserved reward awaits you at the finish line. Every participant will receive a freshly baked, mouth-watering cider donut to refuel after your efforts. But that's not all! You'll also get to enjoy a refreshing beverage from Vitamin Sea Brewing (for those 21+ with valid ID, of course – non-alcoholic options will be available for others) overlooking the ocean with views of Plimoth Rock and the Mayflower II.
Whether you're a seasoned runner aiming for a personal best or looking for a fun way to spend a fall morning with friends and family, the Cider Donut 5K is the perfect event. Enjoy the crisp autumn air, beautiful Plymouth scenery, and the satisfaction of earning your donut and drink!
KID'S RUN 9:15AM
5K RUN 9:30AM
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Sun, Dec 20, 2026 at 9:30 AMSee full details
How could you not love Cousin Eddie? Well, now is your chance to channel your inner Cousin Eddie for our super-fun 5K run honoring the legend himself. Grab your family and friends and join us on Sunday, December 20, 2026 at Mayflower Brewing in Plymouth, MA for the HAP HAP HAPPIEST Christmas run since...well, ever, the 3rd Annual 'Cousin Eddie's Christmas Run 5K'.
Choose to run dressed as Cousin Eddie himself (green bomber-style hat & white robe included with the 'Jelly of the Month Club' registration option), run in our custom Cousin Eddie Christmas Run super-soft T-shirt surrounded by hundreds of other runners dressed as Cousin Eddie, or even sport your own custom costume. Whichever you choose, we guarantee you'll have a ton of laughs!
This run is all about FUN & HAVING SOME LAUGHS while celebrating Christmas and running/jogging/walking with your loved ones!