South Portland

Casco Bay Summer Race Series

For more information on this weekly event, please click here and here.

To see a video on the 2015 Casco Bay Paddleboard Series, click here.

Sat, Jul 23rd,
4:30pm to 8:00pm
Sat, Jul 30th,
4:30pm to 8:00pm
Sat, Aug 6th,
4:30pm to 8:00pm
Sat, Aug 13th,
4:30pm to 8:00pm
Sat, Aug 20th,
4:30pm to 8:00pm
Sat, Aug 27th,
4:30pm to 8:00pm
Annual Event: 

USA Ultimate Southern Maine Invitational

Southern Maine Invitational - USA Ultimate

Come see Maine's best high school USA Ultimate athletes! 

High School Boys and High School Girls 2-day Tourney ~ May 14 + May 15, 2016

Wainright Sports Complex, Gary L. Maietta Way, South Portland, Maine 

Sat, May 14th, 12:15pm to Sun, May 15th, 12:15pm
Annual Event: 

Maine Ultimate Vacationland Tournament

Come visit Vacationland! Maine Ultimate hosts this tournament every summer~

July 21-22, 2018

Wainwright Sports Complex, South Portland, ME

Vacationland will have three divisions: Men's, Women's & Mixed. Registration is $25.00
Cost per team is $500 And here is what you get:
  • Great competition
  • Lined fields
  • Access to trainers throughout the day
  • Finals will be videotaped and possibly livestreamed!
  • Discounted lodging 
  • Saturday night social at Easy Day, South Portland. Music, free food and drink specials. Hang out on the new rooftop deck!

For more information please visit: or contact Richard Young at  




Sat, Jul 21st (All day) to Sun, Jul 22nd (All day)
Annual Event: 

Maine Senior Games - Men's Softball

Maine Senior Games ~ Men's Softball  

Games will be played at the Wainwright Sports Complex, South Portland, Sunday, August 5, 2018.

For schedule and registration information please contact Jo Dill, 207.396.6519,, Southern Maine Agency on Aging.

Sun, Aug 5th, 9:45am
Annual Event: 

Maine Cancer Foundation Twilight Walk Run 5k

Maine Cancer Foundation Twilight 5K - Walk/Run 

Southern Maine Community College, South Portland 

On Thursday, June 7, 2018, hundreds of people will enjoy the Twilight 5K - a family-friendly walk-run fundraising event to support Maine Cancer Foundation. Gather your family, friends, or coworkers together and join the community effort to reduce the burden of cancer in Maine. 

The Twilight 5K is a chip-timed race with mile split times posted on the course. Participants are also welcome to walk the course, and are free to turn around at any point. Remember: every dollar and every step makes a difference!

The Twilight 5K finishes with live music, awards, a pizza party generously donated by Otto Pizza  and a beer tent provided by Shipyard Brewing Company.

Be sure to check out the wonderful sponsors listed who help make this event possible. Register here today!


Thu, Jun 7th,
7:00pm to 8:30pm
Annual Event: 

Santa Hustle Maine 5k & Half Marathon

Santa Hustle® Maine 5k & Half Marathon

Experience the magic of the Santa Hustle® on Sunday, December 3, 2017! 

The Maine Mall

364 Maine Mall Rd 

South Portland, ME 04106 

View Map

If you are a Christmas lover, enjoy overplayed holiday music, devouring candy and cookies, and joining in on an epic after party then grab your favorite friends and family and register for the 2017 Santa Hustle® Maine 5k & Half Marathon!

The 2017 Santa Hustle® Swag is bound to make your jingle tingle even brighter with a Santa Hat, Santa Beard, Santa Shirt, Finisher Medal, and NEW! Candy Cane Socks!

2017 Charity: Easter Seals

The 2017 Santa Hustle Maine Official Charity is Easter Seals.

Easter Seals provides exceptional services to ensure that all people with disabilities or special needs and their families have equal opportunities to live, learn, work and play in their communities. For more information about Easter Seals click here. To make a donation please click here.

Sun, Dec 3rd,
7:00am to 11:30am
Annual Event: 

Maine Ultimate Lobsterpot Tournament

Lobsterpot Tournament, October 21 + 22, 2017

City of South Portland Recreation, Wainwright Farm, South Portland 

Hosted by Maine Ultimate, City of South Portland and Maine Sports Commission

Update: (October, 2017) This year's registration is now closed with 57 teams registered to play in the Lobsterpot Tournament 2017! 

What do you get2 days of some really good ultimate
Lined fields, just like at Nationals. Field lines, players/coaches lines and spectators lines
Tourney Food
A cool tourney central:
Players Lounge, multiple food trucks for lunch, merchandise tents, games

A pretty good party Saturday night!
Winning team of each division gets $1000 cold hard cash!
What would you do with $1000?

Discounted Lodging:

Holiday Inn Express, South Portland

The Holiday Inn Express is centrally located across from the Maine Mall Shopping area.

  • Complimentary wireless internet in all guest rooms and the lobby
  • An indoor pool and fitness center
  • Deluxe Continental breakfast included each morning
  • Our spacious guestrooms are all suites

Contact Information: Rich Young -

Phone number: 207.807.8727 

Update: (October, 2017) This year's registration is now closed with 57 teams registered to play in the Lobsterpot Tournament 2017! 

If you have ever wanted to see Ultimate played OR simply want to come cheer on some collegiate teams, please come join in the fun! 

Sat, Oct 21st, 8:30am to Sun, Oct 22nd, 5:30pm
Annual Event: 

2017 Casco Bay Summer Race Series - Paddleboarding

2017 Casco Bay Summer Race Series

Event Information - 207-317-0425

Weekly Saturday Paddlebard Races  

Race #8, July 22, 2017 - Our half-way point – Mid-series party after the race! Try it out, your first race is free. Each week is a different course wihch will be shared on our Facebook page. 

Registration for the whole season is $60.

LONG (90+ mins) | ??? | BRANDON

Sat, Jun 17th,
4:30pm to 7:00pm
Annual Event: 

Maine Cancer Foundation - Twilight 5K

Maine Cancer Foundation Twilight 5K

On Thursday, June 8th, 2017, hundreds of people will join together to help fight cancer and walk or run one of the most beautiful sunset race courses in Maine at the Twilight 5K

Help the Fight Against Cancer in Maine: Hosted on the breathtaking Southern Maine Community College campus in South Portland, this inspirational event is open to individuals and teams. Each participant can commit to fight cancer through fundraising (Your registration fee will be counted toward your fundraising total).

Enjoy a Walk: You are welcome to run, walk or stroll! Participants may follow a 1.2 mile walk or the full 5K course. What matters most is we're doing our part to help the people of Maine in their fight against cancer.

Or Go for a Run: The Twilight 5K is a chip-timed race with mile split times posted on the course. 

What's a Race without Party? The Twilight 5K finishes with live music, awards, a pizza party generously donated by our sponsors below and a beer tent provided by Shipyard Brewing Company.


  • Online Registration Closes: Wednesday, June 7 at 5pm. 
  • Early Packet Pick-up at Maine Cancer Foundation:
    • Tuesday, June 6 from 9:00am to 7:00pm
    • Wednesday, June 7 from 9:00am to 7:00pm
  • Post Race Activities
    • LIVE Concert with the Mallett Brothers Band!
    • Complimentary post-race Shipyard beer will be served.  You must present an ID to be served beer.  When we see your ID we will give you a bracelet.  You can pick up your bracelet at packet pick up or on race day.
    • Please remember your ID because no ID no beer!  Sorry.
    • We will also have complimentary pizza and Eli’s Rootbeer.
    • Spectators can buy a ticket to the concert which includes beer and pizza for $25.00 at the event.

*Twilight 5K Awards
There will be awards for both men and women the following categories (no duplicates):

  • Top Fundraisers
  • Top 3 overall 
  • Top 3 survivors
  • Age group awards (10 year intervals): 19 and under /20 – 29 / 30 – 39 / 40 – 49 / 50 – 59 / 60 – 69 / 70+

Additional event information and registration steps may be found at:

Maine Cancer Foundation - 170 U.S. Route One, Suite 250, Falmouth ME, (207) 773-2533,    


Thu, Jun 8th,
7:00pm to 9:00pm
Annual Event: 

Santa SUP Paddle

Santa SUP paddle

10 a.m. Dec. 17
Leaves from the boat launch at Bug Light Park, South Portland
Free event!
Santa’s reindeer get him lots of places, but sometimes, the big guy needs to swap Donner and Blitzen for a standup paddleboard. The annual Santa Paddle encourages paddlers to turn up in Santa suits for a group paddle across Portland Harbor and perhaps a stop on Portland’s waterfront for a hot drink. PFDs and winter wetsuits required.

Content provided by Fit Maine who attended last year's event - See the photos on Facebook

Sat, Dec 17th,
10:00am to 12:00pm
Annual Event: