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Friday May 1, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
Saturday May 2, 2026
9:00 AM - 10:00 AM    Instructional Baseball/Softball (K-2) - Instructional Baseball/Softball K-2 Orleans Elementary School - Fields
 
11:00 AM - 4:00 PM    Pop-Up Concerts 44 Main Street Community Building
 
Monday May 4, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
Tuesday May 5, 2026
3:00 PM - 4:00 PM    Spring Youth Tennis in the Parks with USTA - (Grades 2-7) - Fall Youth Tennis in the Parks with USTA - Grades (5 - 7) Orleans Elementary School - Tennis Courts
 
4:00 PM - 5:00 PM    Spring Youth Tennis in the Parks with USTA - (Grades 2-7) - Fall Youth Tennis in the Parks with USTA - Grades (2 - 4) Orleans Elementary School - Tennis Courts
 
5:00 PM - 6:15 PM    Lower Cape Recreational Softball (Grades 2-6) - Spring 2026 - Lower Cape Recreational Softball (Grades 4-5-6): Eastham 2 @ Orleans 2 Orleans Elementary School - Fields
 
Wednesday May 6, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
3:00 PM - 4:00 PM    Spring Soccer Clinic with ACI - (Grades 1-5) - Spring Soccer Clinic with ACI Orleans Elementary School - Fields
 
4:30 PM - 5:45 PM    Field Hockey Clinic - Grades 3-5 - Field Hockey Clinic (Grades 3-5) Orleans Elementary School - Fields
 
Thursday May 7, 2026
3:00 PM - 4:00 PM    Youth Pickleball Clinic - (Grades 4-9) - Youth Pickleball Clinic - Grades 4-9 Eldredge Park Way - Pickleball Courts
 
Friday May 8, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
Saturday May 9, 2026
7:00 AM - 10:00 PM    Chamber of Commerce - Cherry Blossom Festival Orleans Village Green
 
9:00 AM - 10:00 AM    Instructional Baseball/Softball (K-2) - Instructional Baseball/Softball K-2 Orleans Elementary School - Fields
 
11:00 AM - 4:00 PM    Pop-Up Concerts 44 Main Street Community Building
 
Monday May 11, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
6:00 PM - 9:00 PM    Annual Town Meeting Childcare - May 11 - Annual Town Meeting Childcare Nauset Regional Middle School
 
Tuesday May 12, 2026
3:00 PM - 4:00 PM    Spring Youth Tennis in the Parks with USTA - (Grades 2-7) - Fall Youth Tennis in the Parks with USTA - Grades (5 - 7) Orleans Elementary School - Tennis Courts
 
4:00 PM - 5:00 PM    Spring Youth Tennis in the Parks with USTA - (Grades 2-7) - Fall Youth Tennis in the Parks with USTA - Grades (2 - 4) Orleans Elementary School - Tennis Courts
 
5:00 PM - 6:15 PM    Lower Cape Recreational Softball (Grades 2-6) - Spring 2026 - Lower Cape Recreational Softball (Grades 4-5-6): Eastham 1 @ Orleans 1 Orleans Elementary School - Fields
 
6:15 PM - 7:15 PM    Lower Cape Recreational Softball (Grades 2-6) - Spring 2026 - Lower Cape Recreational Softball (Grades 4-5-6): Harwich @ Orleans 2 Orleans Elementary School - Fields
 
Wednesday May 13, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
3:00 PM - 4:00 PM    Spring Soccer Clinic with ACI - (Grades 1-5) - Spring Soccer Clinic with ACI Orleans Elementary School - Fields
 
4:30 PM - 5:45 PM    Field Hockey Clinic - Grades 3-5 - Field Hockey Clinic (Grades 3-5) Orleans Elementary School - Fields
 
Thursday May 14, 2026
3:00 PM - 4:00 PM    Youth Pickleball Clinic - (Grades 4-9) - Youth Pickleball Clinic - Grades 4-9 Eldredge Park Way - Pickleball Courts
 
Friday May 15, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
Saturday May 16, 2026
11:00 AM - 4:00 PM    Pop-Up Concerts 44 Main Street Community Building
 
Monday May 18, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
5:30 PM - 6:45 PM    Lower Cape Recreational Softball (Grades 2-6) - Spring 2026 - Lower Cape Recreational Softball (Grades 2 - 3): Brewster @ Orleans Orleans Elementary School - Fields
 
Tuesday May 19, 2026
10:00 AM - 11:30 AM    Advanced Beginner/Intermediate Pickleball Clinic - May 2026 - Advanced/Intermediate Clinic - Spring 2026 Eldredge Park Way - Pickleball Courts
 
3:00 PM - 4:00 PM    Spring Youth Tennis in the Parks with USTA - (Grades 2-7) - Fall Youth Tennis in the Parks with USTA - Grades (5 - 7) Orleans Elementary School - Tennis Courts
 
4:00 PM - 5:00 PM    Spring Youth Tennis in the Parks with USTA - (Grades 2-7) - Fall Youth Tennis in the Parks with USTA - Grades (2 - 4) Orleans Elementary School - Tennis Courts
 
Wednesday May 20, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
3:00 PM - 4:00 PM    Spring Soccer Clinic with ACI - (Grades 1-5) - Spring Soccer Clinic with ACI Orleans Elementary School - Fields
 
4:30 PM - 5:45 PM    Field Hockey Clinic - Grades 3-5 - Field Hockey Clinic (Grades 3-5) Orleans Elementary School - Fields
 
Thursday May 21, 2026
10:00 AM - 11:30 AM    Advanced Beginner/Intermediate Pickleball Clinic - May 2026 - Advanced/Intermediate Clinic - Spring 2026 Eldredge Park Way - Pickleball Courts
 
3:00 PM - 4:00 PM    Youth Pickleball Clinic - (Grades 4-9) - Youth Pickleball Clinic - Grades 4-9 Eldredge Park Way - Pickleball Courts
 
Friday May 22, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
Saturday May 23, 2026
11:00 AM - 4:00 PM    Pop-Up Concerts 44 Main Street Community Building
 
Monday May 25, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
Tuesday May 26, 2026
10:00 AM - 11:30 AM    Advanced Beginner/Intermediate Pickleball Clinic - May 2026 - Advanced/Intermediate Clinic - Spring 2026 Eldredge Park Way - Pickleball Courts
 
3:00 PM - 4:00 PM    Spring Youth Tennis in the Parks with USTA - (Grades 2-7) - Fall Youth Tennis in the Parks with USTA - Grades (5 - 7) Orleans Elementary School - Tennis Courts
 
4:00 PM - 5:00 PM    Spring Youth Tennis in the Parks with USTA - (Grades 2-7) - Fall Youth Tennis in the Parks with USTA - Grades (2 - 4) Orleans Elementary School - Tennis Courts
 
5:00 PM - 6:15 PM    Lower Cape Recreational Softball (Grades 2-6) - Spring 2026 - Lower Cape Recreational Softball (Grades 4-5-6): Eastham 2 @ Orleans 1 Orleans Elementary School - Fields
 
6:15 PM - 7:15 PM    Lower Cape Recreational Softball (Grades 2-6) - Spring 2026 - Lower Cape Recreational Softball (Grades 4-5-6): Brewster @ Orleans 2 Orleans Elementary School - Fields
 
Wednesday May 27, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
3:00 PM - 4:00 PM    Spring Soccer Clinic with ACI - (Grades 1-5) - Spring Soccer Clinic with ACI Orleans Elementary School - Fields
 
Thursday May 28, 2026
7:00 AM - 10:00 AM    Chamber of Commerce 44 Main Street Community Building
 
10:00 AM - 11:30 AM    Advanced Beginner/Intermediate Pickleball Clinic - May 2026 - Advanced/Intermediate Clinic - Spring 2026 Eldredge Park Way - Pickleball Courts
 
3:00 PM - 4:00 PM    Youth Pickleball Clinic - (Grades 4-9) - Youth Pickleball Clinic - Grades 4-9 Eldredge Park Way - Pickleball Courts
 
Friday May 29, 2026
7:00 AM - 8:00 AM    Early Bird Fitness - Spring 2026 - Early Bird Fitness - May 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Spring 2026 - Adult Pickleball - May 2026 Eldredge Park Way - Pickleball Courts
 
Saturday May 30, 2026
9:00 AM - 10:00 AM    Instructional Baseball/Softball (K-2) - Instructional Baseball/Softball K-2 Orleans Elementary School - Fields
 
11:00 AM - 4:00 PM    Pop-Up Concerts 44 Main Street Community Building
 
Monday June 1, 2026
12:00 AM - 11:59 PM    Boards in the Stores Starts - Chamber of Commerce 44 Main Street Community Building
 
7:00 AM - 8:00 AM    Early Bird Fitness - Summer 2026 - Early Bird Fitness - June 2026 Eldredge Park Way - Pickleball Courts
 
8:00 AM - 11:00 AM    Adult Pickleball - Summer 2026 - Adult Pickleball - June 2026 Eldredge Park Way - Pickleball Courts
 
5:30 PM - 6:45 PM    Lower Cape Recreational Softball (Grades 2-6) - Spring 2026 - Lower Cape Recreational Softball (Grades 2 - 3): Harwich @ Orleans Orleans Elementary School - Fields