Life Happens Outside Day

Life Happens Outside Festival is a celebration of active and outdoor lifestyles in Maine. It provides a day geared towards promoting outside time for teens through interactive activities and entertainment. Proceeds support the Teens To Trails mission to increase the opportunities for teens to experience the outdoors, by providing the resources to start and sustain high school Outing Clubs. Join us at Discovery Park to learn about Maine’s outdoor community and plan your next outing!

Activities will include:
Sterling High Adventure Zone
Climbing Wall
Skills Workshops
Survivalist Demos featuring, Clarence Gilmer, Naked and Afraid; and Zach Fowler, Alone
Mindfulness and Yoga Session
Performances by MAMM students
High Adventure Film Screenings
Maine outdoor non-profits, experience providers, and retailers
Opportunities to gain student volunteer hours
And more!

For more information, please visit:

Fri, Sep 20th, 6:30pm to Sat, Sep 21st, 4:00pm
Annual Event: 

Bikes and Beers Maine 2019

Bikes and Beers is coming to MAINE!! Featuring 15 and 30-mile rides departing from MAINE BEER COMPANY and traveling through the beautiful region of Freeport, ME. All rides will feature rest stops with refreshments

Limited Capacity - Will Sell Out!

Upon return to MAINE BEER COMPANY, riders will receive an official pint glass (and koozie!) with 2 free pours of your choice. There will also be LIVE MUSIC, and lots of outdoor games to play! A Celebration of Cycling and Craft Beer!

Riders will also receive a free raffle ticket for a chance to win several brand new bikes and a ton of other prizes including restaurant gift certificates and cycling gear!

A portion of proceeds from the event will go to the Bicycle Coalition of Maine to help improve the cycling conditions in the Maine. Have fun, and give back! 

Buy your tickets here:

Facebook event:

Sat, Sep 21st,
9:00am to 2:30pm
Annual Event: 

Bradury Bruiser

Bradbury Breaker 

Bradbury Mountain Trail Running Series

September 8, 2019 

A crazy, twisting, turning 12-mile loop of single track-trails filled with rocks, roots, bumps and hills. Save something for the last two miles - this is where you'll earn your bruises! 

Each race is capped at 160 runners and fills fast! 


Sun, Sep 8th,
9:00am to 11:00am
Annual Event: 

Bradbury Mountain Trail Breaker

Bradbury Mountain Breaker 

Bradbury Mountain Trail Runniing Series - the 2nd in a 3 race series 

9 mile course

Event details and course map may be found at Monster Trail Running 

Two laps of an exceptionally hilly, technical single-trail loop that takes you up and down Bradbury Mountain more times than you can count. If you're not begging for mercy on the first lap, you will be on the second! 

Sun, Aug 11th,
9:00am to 11:00am
Annual Event: 

Bradbury Scuffle

Bradbury Mountain Trail Running Series 

Bradbury Scuffle is the 1st in a 3 race series ~ July 14, 2019, Bradbury Mountain, Freeport 

6 mile course - a mix of single and double-track trails with a few rolling hills, a great introduction to Maine trail running. This race is dedicated to Chris Douglass, whose life ended far too soon. 

For complete event details and registration steps for the two other races please visit Trail Monster Series

Bradbury Mountain Breaker - August 11, 2019 - 9 miles

Bradbury Bruiser - September 8, 2019 - 12 miles 



Sun, Jul 14th,
9:00am to 11:00am
Annual Event: 

LL Bean 4th of July 10K Road Race & 1-Mile Family Fun Run/Walk

Online Registration is now closed for the Annual LL Bean 4th of July 10K Road Race and Fun Run

Day of regstration is available! Please see event details below or visit the links provided~ 


Registration Packet Pick-Up

Tuesday, July 2nd and Wednesday, July 3rd, 2019  - 4:00 PM – 7:00 PM 
10K and Fun Run/Walk pre-race registration packet pick-up open in the Old Town Hall at the Hilton Garden Inn.

10K Details

6:00 AM – 7:15 AM 10K and Fun Run/Walk pre-race registration packet pick-up open in the Old Town Hall at the Hilton Garden Inn. 

(Please note: 10K day-of-race registration will end promptly at 7:05 AM.) 

7:05 AM – Race line up begins

7:10 AM – Downeaster Train crosses Bow Street

7:15 AM – Race announcements

7:20 AM – National anthem

7:25 AM – Race starts at the top of Bow Street

7:57 AM – First runners cross the finish line (approx.)

9:00 AM – 10K Award recipients can pick up awards in Memorial Park (approx.)

9:30 AM – Awards ceremony begins in Memorial Park

1-Mile Family Fun Run/Walk Details

6:00 AM - 9:00 AM – Fun Run/Walk registration and packet pick-up open in the Old Town Hall at the Hilton Garden Inn. 

9:00 AM – Line up begins

9:05 AM – Announcements

9:10 AM – Fun Run/Walk starts on corner of Bow Street and South Street

Please visit L.L. Bean 4th of July 10K Road Race site for full event details and registration steps. 

Thu, Jul 4th,
6:00am to 10:00am
Annual Event: 

Close to the Coast 5K & 10K - 2019

The race will be held on Saturday June 15, 2019 at 9:00 am, At Winslow Memorial Park at the end of Staples Point Road in Freeport.  Race and awards are followed by a FREE after race BBQ with FREE food, live band and adult beverage tent from Gritty's for all racers and their families. 

All events rain or shine. Both the 5k and the 10k begin at the entrance of Winslow Park and the course is run on quiet roads and the forest trails along the ocean in the beautiful Park.

The first 500 racers will receive a free custom logo pint glass!!  We have reached the 200 racer threshold for the Free t-shirts.  There will additional shirts available for sale until June 1st for the cost of $10.00.

Online registration ends June 14th at 12:00 pm.  Note, while we are sensitive to issues that may prevent runners from racing; no refunds will be issued after June 1st.

Attentions Walkers:  I get asked the question each year about "Can I walk the course?"  The answer is YES for 5k sign-ups. 

Packet Pick-up/Same day registration opens at 7:00 am and is $25.00 with a possible t-shirt while supplies last.  Same day packet pick-up and registration will be located in the covered picnic area next to the main bathrooms at the Park and will open at 7:00 am.

Pre-Race packet pick-up will be held on June 14, 2019 from 3-6 at Freeport Integrated Health Center, 174 S.Freeport Rd, Freeport.

PRIZES: We pride ourselves on our unique Race Prizes, PIES from Valley View Orchard Pies!

The top 2 finishers overall and in each race category (both 5k & 10k male and female) receive a pie! What better way to enjoy your pie then with your friends and family at a post race barbecue!

Race to Benefit Scholarships!

ALL race proceeds support the Freeport Rotary Club Educational Scholarship Program.  For the past 24 years the Freeport Rotary Club has given over $200,000 in scholarships. Please help us continue this great cause.  


For children, there is a 1K Kids Fun Run will begin at 10:00 am, all children participating in the race receive a prize provided by Wilbur's of Maine. Yum!  No registration required for the fun run.

ITS ALL ABOUT the after party!!   Race is followed by a FREE after race BBQ, with LIVE Band (TBD),  with FREE food and FREE adult beverage tent from Gritty's for all racers and their families. 


Sat, Jun 15th,
9:00am to 9:00pm
Annual Event: 

The L.L. Bean Flannel 5K

The L.L.Bean Flannel 5K – Freeport kicks off at 7:30 a.m. on Sunday, October 20th with packet pickup inside the LL Bean Bike, Boat & Ski Store (57 Main Street, Freeport, ME 04032). Parking is free and plentiful in the city lots on Sundays, but please arrive no later than 7:30 a.m. to ensure you have time to check-in, stretch, and get to the start line, which is a quarter mile away in front of the L.L.Bean outlet store on Depot Street in Freeport Village Station. Packet pickup is from 7:30 – 8:45 AM.

This race is limited to 1,000 runners and completely sold out last year, so sign up ASAP to guarantee your spot!

We will be doing a food donation collection at the race to benefit the Freeport Community Center. Runners may drop off items at the black trailer located outside the registration area. Suggested items include tuna, canned fruit, coffee, granola bars, hearty soups, baked beans, and pasta.

The race starts at 9:00 a.m. on Depot Street and then proceeds gently downhill on Bow Street. Be sure to look on you left for a glimpse of historic Memorial Park complete with Civil War cannons! Turning right onto Lower Mast Landing you will enjoy this sparsely populated road which parallels the Harraseeket River where you might even see Great Blue Herons and Osprey. You’ll eventually turn onto South Street to head gradually back uphill towards Freeport center. The course finishes back on Depot Street by the L.L. Bean outlet store. Be sure to head on back to Discovery Park for the after-race party.

We’ll have pizza, bananas, and drinks for you, but as if that wasn’t awesome enough, we’ll also be giving away L.L.Bean gift certificates (ranging from $25 to $100) to randomly-selected runners!

Registration rates: Early - $25 through May 27, 2019/Regular - $30 - through August 2, 2019/Late - $35 - through October 16, 2019

Please register at LL Bean Flannel 5K

Sun, Oct 20th,
7:30am to 10:45pm
Annual Event: 

Lobsterman Triathlon

With a clear, calm ocean swim, rolling country roads for the bike, and run through pastures and farm stands, The Lobsterman Triathlon offers a one-of-a-kind racing experience. Come check out why so many magazines have named it among the best in America! 

Winslow Park in South Freeport, Maine

Distances: Olympic

  • Swim 1.5 kilometers, Bike 40 kilometers, Run 10 kilometers
  • Swim 1.5K (.93 miles): Starting at the boat launch near the entrance to Winslow park, athletes will do a counterclockwise slightly diamond swim in Casco Bay that finishes on the beach. Average water temperature for September is low to mid-60s, but can be colder depending on the weather leading up to race day.
  • ***Wetsuits: Due to the potentially chilly water, all athletes are required to wear a wetsuit when competing in the Lobsterman.
  • Bike 40K (24.7 Miles): Bike along the scenic coastline of Freeport and Brunswick. Enjoy waterviews, sprawling pastures, and low traffic. The route is a challenging lollipop, with rolling terrain that includes a couple of climbs.
  • Run 10K (6.2 miles): Leave Winslow park and run through the quaint village of South Freeport before returning. The course features closed roads and lots of spectator support! There will be aid stations at approximately every mile with water and lemon-lime electrolyte replacement drink. Some stations will have energy gels and other snacks as well.

Aquabike – A great option for athletes who only want to swim and bike, the Aquabike course is the same as the Triathlon, minus the run! Aquabike athletes will start in one of the waves and race alongside triathletes until the end of the bike. They will dismount their bike and rerack them in Transition, then head out toward the Run. But instead of going left onto the course, they will take a right and run down the Finish Chute. Aquabike athletes will be given a finisher award and provided access to all the post-race areas.

Relays – Team members are required to transfer their chip at their assigned rack space in the Transition Area. The overall time for a relay will be the aggregate of times for each of the members. Specific relay information will be available at packet pick-up.

Please visit for contact, event and registration information. 


Sat, Sep 7th,
8:00am to 12:30pm
Annual Event: 

Betty ReeZ WhoopieZ

Betty ReeZ WhoopieZ
Buck's Naked BBQ 568 US Route #1Freeport,
Sunday, September 23, 2018
Online Registration Close Date & Time. Please see website for course details and additional registration information.  
Friday, September 21, 2018 5:00 PM (EST)
When:                  Sunday, September 23, 2018 @ 9:30 am

Where:                 Buck’s Naked BBQ, 568 US Route 1, Freeport, Maine

Cost:                    Pre-Registration:  $25

                             Race Day Registration:  $30

                             Student Pre-Registration:  $20

                             Student Race Day Registration:  $25

Mail-in Registrations available by contacting


100% net proceeds donated to the Tri-Town Track $ Field Project, benefiting the community, students 
and athletics in the Tri-Town area of Freeport, Pownal and Durham

If race is cancelled due to extreme weather conditions, no refunds~





Sun, Sep 23rd,
9:30am to 11:30am
Annual Event: