| Sunday | Monday | Tuesday | Wednesday | Thursday | Friday | Saturday |
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| 2 | | NAMI Western Massachusetts 19th Annual Walkathon FUNdraiser |
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| | | 5 | | Drop-In ChairYoga & ChairFit Class for Adults |
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| | 12 | | Drop-In ChairYoga & ChairFit Class for Adults |
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| | 14 | | Cycle with All Out Adventures! |
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| | 15 | | Storrowton Village, Opening Day |
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| 16 | | 41st Annual Father's Day Road Race |
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| | 19 | | Drop-In ChairYoga & ChairFit Class for Adults |
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| | 21 | | Cycle with All Out Adventures! |
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| | 22 | | Springfield Dragon Boat Festival 2019 |
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| | 26 | | Drop-In ChairYoga & ChairFit Class for Adults | | Rainbow Support Group | | Jericho Rock and Roll Dance |
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| | 28 | | Cycle with All Out Adventures! |
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