Portland Brewers Holiday Dash 5K ~ Portland Trails

A festive favorite to kick-off your holiday season! 
December 11th ~ 11am

Join Portland Trails & Ri Ra Irish Pub for a Portland holiday tradition, featuring local craft brews! Run the trails in your festive gear, and enjoy a hearty beer-brunch with some winter cheer. We will run (and brunch) through snow, shine, wind or sleet!

Race starts at 11am, with a hearty brunch by RiRa Irish Pub to follow. If you love the trails in Portland, come on out and celebrate and support us!


Eastern Promenade – RiRa Irish Pub
$35 – Includes brunch, and local craft beer ticket!
Holiday Dash Race Course

Please note, this race will take place, rain, shine, sleet or snow! Be prepared!

  • Who can participate in Holiday Dash?We welcome all runners and walkers to participate. You must be over 21+ to consumer beer at brunch.
  • What is included in my registration?All runners will get access to free brunch, and 1 beer ticket included with registration. You also get a t-shirt. This race includes automatic timing and water stops halfway through and at the end of the course.
  • When does registration open? Online registration opens Friday, September 16 at 8am and runs until the race sells out. We encourage participants to sign up early, we sell out every year.
  • Do I get a race shirt.Cotton race t-shirts are available for all runners/walkers. Sizes depend on availability.
  • Can I run with  my dog? What about strollers? Because of the number of people out on the race course we cannot allow dogs or strollers.
  • What awards do you have? Awards will be given to the top male and female finishers, and top Portland Trails members, male and female.
  • I’m not running this year, but I’d like to support the trails! Sign up HERE to volunteer.


Sun, Dec 11th,
11:00am to 1:00pm
Annual Event: 

Portland Thanksgiving Day 4 Miler

Portland Thanksgiving Day 4-Miler

9 a.m. Thanksgiving Day, Nov. 24. Starts on Congress Street, Portland. $20. www.facebook.com

We all have our Thanksgiving traditions (dinner at aunt Betsy’s, binge-eating mashed potatoes and helping dad untangle the Christmas lights, for example). The Thanksgiving Day 4-Miler through downtown Portland is another of those traditions.

Bring non-perishable food to benefit Project FEED. 

Keep those holiday traditions going! 

Thu, Nov 24th,
9:00am to 11:00am
Annual Event: 

Portland Waterfront 5K

Saturday, November 12, 2016 - 10am
Location: Flatbread Company, 72 Commercial StreetPortlandMaine
Created By: 5K Sports Race Management
See website for various registration fees to including Flatbread pizza and salad, T-shirts - it's runner's choice! 
Buffet to include Flatbread pizza, salad & cash bar " The very best pizza that we can imagine"

  *  First 74 runners receive a race beverage glass, custom race bibs, overall top male & female, overall 

     top age group, 1-14, 15-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-99. 

  *  Long sleeve technical shirts are $10.00 extra  Need to register by 10/29/16  NO technical shirts on race day 

  *  On Line Course Map-  Course- Race runs along Portland Trails near Commercial Street.  Starts and

      finishes by Casco Bay Lines Ferry Terminal 

  *  3D Flyover Video

  *  If race is cancelled because of weather extreme conditions, NO REFUNDS  

  *  Map Quest

     2014 RESULTS

     2015 RESULTS
Online Registration Close Date & Time
Friday, November 11, 2016 6:00 PM (EST)
Sat, Nov 12th,
10:00am to 2:00pm
Annual Event: 

Lyseth Trails for Technology 5k

Lyseth Trails for Technology 
November 5, 2016
Lyseth Trails for Technology 5K Walk/ Run is a family friendly event. The course winds through quiet, less traveled roads of Portland's  North Deering Neighborhoods.  Walkers and runners alike will enjoy the community feel as neighborhood residents come out to cheer us on!  
Welcome back for our 3nd annual event. Our first Walk/Run was a great success. We had over 200 entries and it was a great community event. Come out and join us again this year. Bring all of your friends and family. We have expanded the field to greater than 300. Sign up now to ensure your place in this years fun filled event.

Support technology improvements in Lyseth classrooms! Our host, the Lyseth PTA, strives to augment the already stretched school budget and we need your help!
Come out and enjoy this fun, family, community walk/run in Portland's quiet North Deering neighborhood.  Kids (grades K - 5)  1/2 mile fun run starts at 9:30am (free to all participants), followed by 5K walk/run at 10am. Music, prizes and raffles to follow!

More event information may be found at http://lysethtechnology5k.weebly.com
Sat, Nov 5th,
9:30am to 12:00pm
Annual Event: 

Old Port Pub Run

Old Port Pub Run ~ Meet up at Liquid Riot

November 3rd at 6:15pm

Free group run every Thursday at 6:15pm with after-run libations at Liquid Riot. 

I Run.Drink.Socialize

FMI: www.facebook.com/oldportpubrunME

Thu, Nov 3rd, 6:15pm
Annual Event: 

Dispatch Magazine 5K Road Race

 Dispatch Magazine 5K Road Race ~ October 30, 2016

This is a short, fast, course around Portland’s beautiful Back Cove (seriously, have you SEEN the Back Cove in autumn?) Take advantage of that cool fall air, smash your previous 5k PR, and enjoy the scenery before we plunge into “trapped-on-the-dreadmill” season.

Never run a 5k before? This is your chance! Exercise isn’t that scary, even on Halloween.

– First 150 registrants get a free Sport-Tek tee!
– Prizes for top 3 male/top 3 female finshers!

*REGISTER HERE: http://bit.ly/2bdwPXq

Costumes welcome, fun guaranteed, and remember – we’re helping to raise funds for our friends at WMPG community radio! http://bit.ly/2b54C3E

*Bib pickup is Saturday, October 29 at Fleet Feet Maine, 309 Marginal Way, Portland*

FMI: www.facebook.com/events/1635750070071562/


Sun, Oct 30th,
11:00am to 6:00pm
Annual Event: 

Insane Inflatable 5K Obstacle Course


The Insane Inflatable 5K is coming to your neck of the woods! Get ready to experience the most fun, wild and insane obstacle run in the world. Get “pumped up” for a course filled with the world’s largest and most extreme inflatable obstacles ever produced. Here’s your chance to be a kid at heart, and insane by choice!



Read More: Insane Inflatable 5K Obstacle Fun Run - Portland, ME | Insane Inflatable 5K | http://insaneinflatable5k.com/maine/?trackback=tsmclip



$49 July 8, 2016
$54 July 22, 2016
$57 August 12, 2016
$60 September 2, 2016
$65 September 16, 2016
$75 Event Day Only
$100 ALL ACCESS PASS (Sign up for any wave time, even if it is full.)





Team registration is available and encouraged — get your friends, co-workers, gym buds and more to join you at this year’s most insane obstacle run! The largest team will be immortalized on our Facebook page and we encourage you to get insane with your team costumes. Team Captains get some really cool incentives!




Go Big or Go Home! The Insane Inflatable 5K offers individuals the chance to register for the “All Access Pass,” giving them the ability to run in any wave time, even if that wave is sold out. The All Access Pass comes with a special wristband color (handed out at packet pickup), which allows you to enter the starting line corral for any wave time you choose. In addition, it also gives you a $20 merchandise credit to get some sweet swag at our on-site merchandise tent.

Most of our events sell out and often times people do not get to run in the waves their friends are running in. The All Access Pass gets you into the wave with your friends even if it’s sold out. For all you procrastinators out there – you’re welcome!




Insane Inflatable 5K is proud to announce that we have partnered with the American Cancer Society to benefit their Relay For Life movement.

About The American Cancer Society

American_Cancer_Society_LogoThe American Cancer Society is the nationwide, community-based, voluntary health organization dedicated to eliminating cancer as a major health problem by preventing cancer, saving lives, and diminishing suffering from cancer, through research, education, advocacy, and service.

The American Cancer Society is thrilled that the Insane Inflatable 5K has chosen the organization as their charity of choice for their 2016 events. A portion of the proceeds from each Insane Inflatable 5K will support the local Relay For Life event in each community in which an Insane Inflatable 5K event is held.

Make a donation to the American Cancer Society and enable the Society to help people facing the disease today, educate people about how to reduce their risk for cancer or detect it early when it’s the easiest to treat, and fund cancer research that will help protect future generations.

How Can You Help? Add a Few Bucks When You Register!

When you register for the Insane Inflatable 5K, why not add a donation to your checkout price? We promise, and are committed, to make sure that money directly funds the American Cancer Society Relay For Life movement in your city.

Additional event details including course description and volunteer opportunities may be found on the website. 
Read More: Insane Inflatable 5K Obstacle Fun Run - Portland, ME | Insane Inflatable 5K | http://insaneinflatable5k.com/maine/?trackback=tsmclip

Sat, Sep 17th,
8:30am to 4:00pm
Annual Event: 

Casco Bay Islands SwimRun



Enjoy the beauty of Casco Bay and a very special perspective of the race from the deck of the classic schooner Wendameen or the WWII naval launch, the Elizabeth Grace. Departing Portland early, and a quick stop at Peaks Island for any athletes' family and friends who are staying there, you'll cruise up to Chandler's Cove for the 7AM start, maybe while enjoying your first coffee (BYO) as the sun rises above the islands and follow along much of the course from the water taking in 7 of the 9 swim legs and a couple of shore scrambles.Passengers will disembark  at Peaks Island by 10:30 to see teams cross the finish line. Limited capacity is available so don't delay. Be sure to bring foul weather gear in the event of....foul weather.  Tickets are also separately available for the finish line lobster bake on Peaks Island. Half of the ticket cost will directly benefit the Travis Mills Foundation, our beneficiary partner!  www.travismills.org

Select the "Store" tab at the top of the green menu choices to the left to complete these purchase options.

Sponsor and Spectatator Opportunities!!

Exceptional Sponsor and Spectator offers are described in the attached brochure. Be part of the finish line festivities and a Peaks Island Lobster Bake!!

On April 10, 2012, United States Army Staff Sergeant Travis Mills of the 82nd Airborne was critically injured on his third tour of duty in Afghanistan by an IED (improvised explosive device) while on patrol, losing portions of both legs and both arms. He is one of only five quadruple amputees from the wars in Iraq and Afghanistan to survive his injuries. His foundation is creating a national retreat to help veteran families unite with the land, water, nature and each other to revitalize themselves and to keep moving forward. The retreat will be uniquely designed to provide state-of-the-art “smart home” technology in a relaxed lodge setting. It will fill a vital role in recovery, camaraderie, spousal support, re-connection, and reintegration. Veteran families from all over the United States will enjoy a week of swimming, boating, fishing, site-seeing, campfires, adaptive sports, and much more.We are honored to announce that the Travis Mills Foundation has become our Official Beneficiary Organization. Take a moment through the image link below to acquaint yourself with this selfless American hero who lives every day by the inspiration....“Never give up. Never quit.”

In conjunction with this announcement, five NEW Travis Mills Foundation Team slots have been established. The first five teams that will contribute $1,000 to the Travis Mills Foundation will be awarded a guaranteed team slot in the August 14 event to be held among the Casco Bay Islands in Portland Maine. 125 team slots were filled in less than three weeks from among more than 600 applications for the race consisting of nearly 12 miles of run/trekking and 4 miles of swimming. Complete event information can be found at www.usa-swimrun.com. Interested teams should consult the site for rules and qualifying standards that must apply with respect to open water swimming capabilities. The team race fee of $400. will apply in addition to the tax deductible contribution to the foundation.

Registration for the Travis Mills Foundation Team slots will open on April 20, at Noon EST.


Inspired by the preeminent, international Swimrun race series OTILLO ("island to island), originating in Sweden in 2006, two multisport veterans looking for the next adventure are excited to introduce the first "OTILLO- style" Swimrun event in the US. Consisting of multiple, alternating swim and overland running legs (island roads, trails, and shoreline scrambles) between 8 islands in Portland, Maine’s spectacular Casco Bay, SwimRun will test competitors with run legs across nearly 10 miles of varied island island terrain and a combined 4 miles of open water swimming.

Remaining true to the originators of the OTILLO, Casco Bay Islands Swimrun is a two-person team event. Not a relay, teamates must race the entire course together. Rules permit swim aids such as hand paddles, pull buoys, wetsuits and even swim fins to name a few. Certain safety gear is mandated by race rules, as is being tethered during the swim, and hydration and race fuel is typically carried too, but what one starts with, so too must they finish. Changing from trail shoes to swim fins, or tending to awkward gear can chew up valuable time. Having the right teammate and equipment can make all the difference.

Information on how teams will be selected for one of the 100 slots is detailed at Event Info.

Hopefuls are encouraged to visit the official OTILLO website and the Official Film: OTILLO 2015 The Swimrun World Championship to learn more about this challenging event and gain insight on optimal gear selection. Casco Bay SwimRun is produced by Valhalla Sports Group and USA-SwimRun. The event is not an OTILLO affiliated event and is not associated with the official OTILLO brand.

2016 Team Selections Finalized

Listing of the finalized team selections for the 2016 Casco Bay Islands SwimRun. They come from all over!!  Welcome to the party! 

Sun, Aug 14th,
7:00am to 5:00pm
Annual Event: 

Port Mile Swim Benefit

Port Mile is a one mile open water ocean swim to benefit the nonprofit Friends of Fort Gorges.


FMI - https://runsignup.com/Race/ME/Portland/PortMile

Sat, Aug 13th,
7:00am to 8:00am
Annual Event: 

Three Day Casco Bay Traverse

This three-day guided expedition begins in Portland and ends all the way on the other side of Casco Bay in Phippsburg. Along the way, we’ll camp on two islands and experience the diverse environments found in the bay — from the exposed ocean-like conditions along the outer islands to the calm and peaceful estuaries of the inner waters. Our route will depend on the conditions and the group, but you can plan to do a significant amount of paddling as we traverse the bay. Sea kayaking experience is required. Portland Paddle will provide all meals and paddling gear. The group will be picked up at the end of the trip and driven back to Portland. Upon booking you will receive a packet with a more detailed itinerary and packing list. $358 per person.

FMI: portlandpaddle.net

Fri, Aug 12th (All day) to Sun, Aug 14th (All day)
Thu, Aug 25th (All day) to Sat, Aug 27th (All day)
Annual Event: