| Date | Event |
| June 4 | National Trails Day Events Cancelled due to disaster relief efforts throughout the area |
| June 4 & 5, 2011 | Molly Cromwell Presents: Sturbridge Dollhouse Miniatures Festival Features international craftsmen Sturbridge Host Hotel $6 adults $4 children |
| June 4 | Bethlehem Lutheran Church Fun Fair 9:30 AM to 4:30 PM On the Sturbridge Common |
| June 4 | Antique Car Rally at Old Sturbridge Village |
| June 4, 5 | Sturbridge Police Department Boating Safety Course Ages 12 and up 9 am to 2 pm both days (both days are required) Registration: (508) 759-0002. |
| June 4 | Quinebaug Valley Singers Concert: The Shining River St. Anne's Shhrine 7:30 pm |
| June 11 | Socks for Siberia Family Festival Hyland Orchards - Arnold and Lake Roads Noon to 6 pm |
| June 13-16 | Rehabilitative Resources Inc Indoor Flea Market and Yard Sale at Rehabilitative Resources, 1 Picker Road, Sturbridge, MA. $40 per day or $80 for all four. Proceeds to support historic Elm Hill Center in Brookfield. More info: 508-347-8181x107 |
| June 17 - July 10 | Stageloft Repertory Theater presents Annie Get Your Gun Friday & Saturday @ 8 pm
Sundays @ 2 pm
ADDED PERFORMANCES: Sat June 25th - 2 PM and Thurs July 7 - 8 PM
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| June 17-19 | Disc Jam at Hyland Orchards Camping, food, live music and disc golf Great way to spend Father's Day weekend |
| June 17-18 | Relay for Life - participants from surrounding towns walk the track at Southbridge High School to raise funds for cancer research and treatment |
| June 23 | Fine Art/Antique Appraisals with Kaminski Auctions Sturbridge Host Hotel 10:30 am - 12;30 pm - bring up to 3 items to be appraised |
| June 24 | Annual Muster on the Common 6:30 pm Sponsored by the Sturbridge Historical Society |
| June 24 | Rehabilitative Resources Inc. Annual Charity Golf Classic at Blissful Meadows Golf Club in Uxbridge, MA |
| June 24-26 | Tantasqua Regional High School Class of 1961 50th Anniversary Reunion Info: (508) 248-7845 |
| June 25 | Live music at The Copper Stallion: New Pilot 10 pm to closing Main Street/Route 20 |
| June 25 | Chowder Fest at Pioneer Brewing $10/person Located at the corner of Arnold and Lake Roads |
| June 25 | Tornado Relief Fund Raiser: Golf at Heritage Country Club Starts at 1 pm More info on web site |
| June 26 | Molly Bish Motorcycle Ride - ride starts at noon Annual Molly's Ride for Child Safety Contact: Ron Gresty, e-mail gresty@verizon.net This year's location: Center at Hobbs Brook
100 Charlton Rd (Rt. 20) |
| June 28 | Taste of Tourism and Mega Networking Event at Old Sturbridge Village 5 to 7:30 pm Sample food, wine and beer at this offering from local chefs $10 advance/ $15 at door Also, free culinary seminar at 4 pm Online auction: www.biddingforgood.com/CMCVB |
| Throughout the Month | Relay for Life Events |