| Date | Event |
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| May 1 | Sturbridge Lions All American River Race http://www.angelfire.com/ma3/sturbridgelions/events.html |
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| May 1 | Lucky Duck Day at Westville Recreational Area 11 am to 2 pm $5 for one duck |
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May 6- 20, 2011 | Stageloft Repertory Theater presents Hamlet - a Tragedy Fri and Sat at 8 pm Sun at 2 pm Call (508) 347-9005 for ticket reservations |
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| May 6 | Open House • The New Whistling Swan Restaurant
5:30-8:00pm |
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| May 6 | Live Music at the Sturbridge Coffee House: Josh Siok 7 pm Main Street/Route 20 |
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| May 6 | Live Music at the Ugly Duckling Loft: Rob Adams 7 pm Main Street/Route 20 |
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| May 7 | Live Music at Rovezzi's: Rob Adams 6:30 pm Main Street/Route 20 |
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| May 8 | Mother's Day - order flowers from one of our local florists or take mom out for brunch at one of our spectacular restaurants. Also, free admisson for Mothers at Old Sturbridge Village. |
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| May 9 | The Publick House Cooks: Fundraising Dinner for Boy Scouts and Sturbridge Lions Club Italian Buffet with seatings at 4:30 PM and 6:15 PM Adults $13, kids 4-15 $5 |
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May 9 | Vintage Fashion and Textile Show Sturbridge Host Hotel http://www.vintagefashionandtextileshow.com/press.html |
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| May 10 - 15, 2011 | Brimfield Antique Show www.brimfield.com |
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| May 11 | Women in Business Annual Scholarship Auction Publick House Historic inn Proceeds go to WIB Scholarship Fund Registration starts at 5 pm More info: (508) 764-1657 |
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| May 14 | Margarita and Mexican Beer Tasting Sponsored by the Sturbridge Optimist Club $25 per person Proceeds help to fund projects for children Held at Admiral TJ O'Brien's on Main Street/Route 20 7 to 9 pm |
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| May 14-15, 21-22 | Sturbridge American Legion Baseball Tryouts Must be born after January 1, 1992 Info: (508)425-9698 |
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| May 15 | Pioneer Brewing 7th Anniversary Party! (508) 347-7500 |
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| May 15 | Tantasqua's Annual Wag n' Walk for Second Chance Animal Shelter Noon to 4 PM on the trails at Tantasqua Regional High School More info: (508) 867-5525 |
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| May 17 | |
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| May 17 | Small Business Workshops at the Sturbridge Host Hotel 8:30 am to 1:30 pm: Small Business Conference - including social media 1:30 pm to 6:00 pm: Business/Consumer Expo Register online at QHMA.com or call (413) 967-3001 |
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| May 21 | Tomato Plant Giveaway - free tomato plant with admission to Old Sturbridge Village, while supplies last, from 2 to 5 pm |
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| May 25 | All Arts Day at Tantasqua Regional High School View artwork by students of all grades from 6:30 - 8:30 pm |
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| May 26 | Sturbridge Historical Society Meeting 7 pm Publick House Historic Inn Main Street/Route 20 |
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| May 27 | Community Business Associates program on personal development, with speaker Dennis McCurdy. Topic: Going All Out. 7:15 am at Oliver Wight Tavern. More info: www.communitybusinessassociates.org |
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| May 27 | Veterans Breakfast at Tantasqua Junior High School 8 - 9 am Memorial Ceremony 9 - 10:30 am Reservations for breakfast: (508) 347-7381 |
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| May 27 | Annual Memorial Day Ceremony at Burgess Elementary School 1:30 pm |
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| May 27 | Grave decorating session at American Legion Hall Main Street/Route 20 6:30 pm |
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| May 28 | BB 5K Race Festival to Follow the Race! 9 AM Hyland Orchard - Arnold and Lake Roads Benefits Myeloma Research and Education |
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| May 29 | Memorial Day service, Sturbridge Federated Church 8 Maple Street 10:15 am |
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| May 30 | Memorial Day Parade 9:30 AM Starts at corner of Routes 20 and 148 Ends at Town Common on Route 131 |
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| May 30 | Memorial Day Dance hosted by the Hayloft Steppers Square Dance Club 232 Podunk Road Early rounds start at 1:30 pm $7/person More info: (508) 867-8036 |
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| May 31 | Memorial Day |
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