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Million Mile 2019

September 1 @ 12:00 am – September 30 @ 12:00 ameverywhere

The Million Mile 2019 will take place from September 1 through September 30, 2019. This is a virtual event, so people can participate wherever they live. The Alex’s Lemonade Stand Foundation for Childhood Cancer (ALSF) is the organizer of this event which coincides with Childhood Cancer Awareness Month. The event is presented by Volvo,  and Aldi is the gold sponsor. Participants are asked to keep track of the miles they log during the month of September by walking, jogging, running,…Find out more »

Housatonic Heritage Walks 2019 1st Weekend

September 7 – September 8Free

The Housatonic Heritage Walks series will begin Saturday and Sunday, Sept. 7 and 8, 2019. This is the first of four consecutive autumn weekends of events sponsored by the Upper Housatonic National Heritage Area (Housatonic Heritage). Organizers have assembled an ambitious 71 events spread over the four weekends, involving more than 20 towns stretching from Hinsdale, MA in Berkshire County  to Salisbury, CT in Litchfield County.  There are 20 events scheduled for the Sept. 7 – 8 weekend. The remaining…Find out more »

Woofstock 2019 5K and Dog Walk

September 8The Common on First

The Woofstock 2019 5K and Dog Walk will be held Sunday, Sept. 8, 2019 at The Common on First St., Pittsfield, MA  01201. The event is organized by the Berkshire Humane. The Dog Walk includes a 5K Run and  more formalized Canine Games. These events are part of a larger family-oriented Festival . The Dog Walk route is approximately one mile long. Timing for the 5K is by Berkshire Running Center. Besides the entry fee, participants are encouraged to fundraise.…Find out more »

September 8Olana State Historical Site

The Barry Hopkins 12th Annual Run at Olana, will be held Sunday, September 8,  2019 at Olana State Historical Site, Wagon House Education Center, 5720 Rt 9G, Hudson, NY 12534. This 3.8 mile run and Children’s run is a collaboration between the Olana Partnership and the Onteora Running Club. The entry fee is $15 for members and $20 for non-members. Children are free (but no T shirt). Free T shirts to first 75 registrants. For registration form  go here: http://www.onteorarunners.org/wp-content/uploads/2019/03/barry-hopkins-Application.pdf…Find out more »

Community At Bat 3rd Annual Charity Softball Game

September 8Memorial Field Park

The Community At Bat 3rd Annual Charity Softball Game will be held Sunday, September 8,  2019 at Memorial Field Park, Bridge Street, Great Barrington, MA  01230. The entry fee for the event, which is open to the public, is $20 per person. Pre register at cdcsb.org/communityatbat. Effort will be made to match registrants with their correct T shirt size. There will be free SoCo ice cream, free E-bike rides, live WSBS radio coverage, and great online and day of raffles.…Find out more »

Kent Volunteer Fire Department Golf Tournament

September 9Bulls Bridge Golf Club, 71 Bulls Bridge Road
South Kent, CT 06785 United States + Google Map$250

The Kent Volunteer Fire Department Golf Tournament will be held Monday, September 9, 2019 at the Tom Fazio-designed Bulls Bridge Golf Club, 71 Bulls Bridge Road, South Kent, CT  06785. The rain date is Monday, October 7th. The 18 hole tournament will be a four-person scramble format. There will be on-course contests including  a hole in one prize. The cost of the event is $250 per person which includes green fees, cart, light lunch, on-course refreshments, prizes, awards and three-course…Find out more »

Sharon Fire Dept. Annual Golf Tournament

September 10Sharon Country Club

The Sharon Fire Dept. Annual Golf Tournament will be held Tuesday, Sept. 10, 2019 at the Sharon Country Club,  Amenia Union Road, Sharon, CT  06069. Rain date is Sept. 17th. The entry fee for the 18 hole, four-person scramble event is $135 per person which includes green fees, cart, lunch, on-course contests, refreshment cart, awards and dinner. There will be a raffle. On-course contests include closest to the pin, longest drive and hole in one. Pre-registration is required, but register…Find out more »

Chad Malarchuk Memorial Golf Tournament

September 13 – September 14Undermountain Golf Course, 274 Under Mountain Rd
Copake, NY 12516 United States + Google Map

The Chad Malarchuk Memorial Golf Tournament will be held Saturday, September 14, 2019 at Undermountain Golf Course, 274 Undermountain Road, Copake, NY 12516. The event is hosted by  the Undermountain Golf Course. The entry fee for the 18 hole, two-person scramble is $100 which includes green fees, cart, prizes, lunch, dinner and beverages. There are two shot gun start times. The deadline for mail in registration is Sept. 1st. To get a registration form email service@undermountaingolf.com. Make checks payable to…Find out more »

Housatonic Heritage Walks 2019 – Weekend 2

September 14 – September 15Free

The Housatonic Heritage Walks 2019  series continues with its second weekend, Saturday and Sunday, Sept. 14 – 15, 2019 with 17 events involving  towns in Berkshire County Massachusetts to Litchfield County Connecticut. 20  events were held last weekend, Sept. 7 – 8. The remaining events will be held on Sept. 21 – 22 and Sept. 28 – 29. All of the events, sponsored by the Upper Housatonic Heritage Area, are meant to showcase the many natural, historic and cultural treasures…Find out more »

Hamzy’s Ketsu-ka Karate Tournament of Champions

September 14St Peter/ St Francis School

Hamzy’s Ketsu-ka Karate Tournament of Champions will be held Saturday, Sept.14, 2019 at the St. Peter/St. Francis School gymnasium, 360 Prospect St., Torrington, CT 06790. The event is sponsored by Hamzy’s School of Self Defense and Executive Director and Grand Master  John S. Hamzy. The ‘best of the best” will assemble from all over the United States and Puerto Rico to  compete for the top designation. A full spectrum of categories will be represented ranging in ability from beginner to…Find out more »

Macedonia Trail Race

September 15Macedonia Brook State Park

The Macedonia Trail Races will be held Sunday, September 15, 2019 at Macedonia Brook State Park, 159 Macedonia Brook Road, Kent, CT 06757. New this year- both  25K and 50K races have been added along with the 7.25 mile race. The event is organized by Steep Endurance. Entry fees: 7.25 mile $35 through June 30 $40  July 1 – Aug. 31 $45  Sept. 1 – Race Day 25K $60  through June 30 $65  July 1 – Aug. 31 $70  Sept.…Find out more »

Josh Billings RunAground Triathlon

September 15Stockbridge

The 41st Annual Josh Billings RunAground Triathlon will be held Sunday, September 15,  2019 beginning at the Price Chopper parking lot in Great Barrington, MA and ending at Tanglewood in Lenox, MA. This is the 43rd running of the Josh, and although organizers had to rearrange the route last year, this year it is back to its original route. The triathlon is named after a famed 19th Century humorist who lived in the Berkshires. The event reflects Mr. Billings not-too-serious…Find out more »

Lakeville Open Horse Show

September 15Riga Meadow at Coole Park Farm

The Lakeville Open Horse Show will be held Sunday, September 15, 2019 at Riga Meadow at Coole Park Farm, 1031 Bangall  Amenia Road, Millbrook, NY 12545. This is a rain or shine event. There will be refreshments for sale. Admission is free, funds are raised through entry fees for competitors. Entry fees for the many classes range from $10 – $25. Pony club members receive a discount. Add $5 per class after Sept. 9th. To find mail-in entry form go…Find out more »

John F. Foley Lone Oak Challenge Annual Golf Tournament

September 16Egremont Country Club

The John F. Foley Lone Oak Challenge Annual Golf Tournament will be held Monday,  September 16,  2019, at the Egremont Country Club, 685 S. Egremont, MA 01230. The entry fee for the 18 hole, four-person, best ball scramble format tournament is $125 per person which includes green fees, cart, lunch , on-course contests, awards and dinner. There will also be a putting contest and 50-50 holes. On-course contests include closest to the pin, longest drive and  hole in one opportunity…Find out more »

Salisbury Central School 7th Annual Golf Tournament

September 19Hotchkiss School Golf Course

The Salisbury Central School 7th Annual Golf Tournament will be held Thursday, Sept. 19, 2019 starting at 8:30 am at the Hotchkiss School Golf Course in Lakeville, CT. Registration begins at 7:45 am. The rain date is Sept. 26th. The entry fee for the 18 hole, four-person scramble format event is $400 per foursome which includes green fees, cart, coffee and donuts, on-course snacks and beverages, lunch, on-course contests and awards. On-course contests include closest to the pin and longest…

Hearts of the Father Outreach 13th Annual Golf Tournament

September 19Wyantenuck Country Club, 46 W Sheffield Rd
Great Barrington, MA 01230 United States + Google Map

The Hearts of the Father Outreach 13th Annual Golf Tournament for the Orphans will be held Thursday, September 19  2019 at the Wyantenuck Country Club in Great Barrington, MA 01230. Entry fee for the 18 hole, four-person shamble format (players pick longest drive of the four, then play their own ball) event is $125 per person for Wyantenuck members and $155 for non-members. There is a dinner only option for $35. Fee includes green fees, cart, on-course refreshments, bag lunch,…Find out more »

9th Annual Walk a Mile in Her Shoes – Pittsfield

September 19North St. Pittsfield

The 9th Annual Walk a Mile in Her Shoes – Pittsfield will be held on Thursday, September 19, 2019, corner of North Street and Columbus Ave, Pittsfield, MA  01201. The event is organized by the Elizabeth Freeman Center. This one mile walk is free to whoever cares to join in, but many will solicit donations in advance of the event. Raise $55 in donations and receive a 2019 Walk a Mile T shirt. To register online or find a mail…Find out more »

The Salisbury Winter Sports Association (SWSA) 12th Annual Golf Tournament and Pig Roast

September 20 – September 21Under Mountain Golf Course

The Salisbury Winter Sports Association (SWSA) 12th Annual Golf Tournament and Pig Roast, Saturday, September 21, 2019 at the Under Mountain Golf Course in Copake, NY. The rain date is Sunday, Sept.22nd . Participants in the two- person scramble event can choose between two nine-hole flights or an 18 hole event. The tournament day schedule is as follows: 10 am First flight registration, breakfast sandwiches for sale 11 a.m. First flight shotgun start for morning 9 hole and 18 hole…Find out more »

Falls Village Food and Truck Fest

September 21

The Falls Village Food and Truck Fest will be held Saturday, Sept. 21, 2019 at the Falls Village Recreation Center, 108 Route 63, Falls Village, CT 06031. This event was previously known as the Falls Village Truck Pull. Rain date is Sunday, 22nd. The event features Craft Breweries and Wineries, Food Trucks, Truck Show, SPI Truck Pull, Live Band and Vendors. The Truck Pull will feature four classes: Enhanced Gas, 2.5 Limited Pro Stock Diesel Super Stock Gas Powder Puff…Find out more »

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