Enter for a chance to win 4 passes to Urban Air Trampoline and Adventure Park in Bellingham. 

Enter for a chance to win 4 tickets to the Boston Red Sox game on Thursday, May 7th vs. the Rays at 7:10pm. 

Win 4 tickets to the Discovery Museum in Acton, MA! Discovery Museum is a hands-on museum for families that blends science, nature, and play. Admission includes access to both the museum and the Discovery Woods outdoor nature playscape and gigantic treehouse.

TreeTop Adventures is a high ropes and obstacle course located in Canton, MA. Opportunity for adventure is limitless at TreeTop Adventures! Enter to win one ticket to TreeTop Adventures, for ages 7+. Retail value $71.

Win a 3-class pack ($90 value) to Rev'd Indoor Cycling

Gift Certificate worth $100 off a class sign-up at Create Roslindale

Win one free week of half-day summer camp ($250 value) at West Roxbury School of Dance

Win a private wine class for 20 people ($600 value) at Total Wine in Dedham

Free Family Mini Session with Katherine Teahan Photography Includes:
- A 30-minute family session
- A minimum of 15 edited digital images
- Session must be scheduled and completed by December 31, 2026

Ready for Spring? Win 5 yards of mulch with free delivery from Minuteman Landscape Supply in West Roxbury

Win a gift certificate for a family membership to the Larz Anderson Auto Museum $150 value (two family memberships available)

Win 4 mini golf passes to Starland Sportsplex and Fun Park in Hanover

Gift Certificate for attendance at Summer Fun Dance Workshop (July 27-31 or August 3-7 from 9:00am-12:00pm) at Julianne's Dance Workshop in West Roxbury. $180 value.

$100 gift card to American Flatbread Bowling/Pizza in Brighton

$25 gift card to Ron's Gourmet Ice Cream and Bowling Hyde Park

4 mini golf passes ($52 value) to Monster Mini Golf

2 passes to the Explorer River Tours at Blackstone Valley in Rhode Island ($80 value)

Enter for a chance to win a $75 gift card to Boston Ale House in West Roxbury

Enter to win a $25 gift card to Joe's 320 Cafe in West Roxbury. Two gift cards available.

$50 Gift Card to Few & Far/Satellite Bottle Shop in Dedham.

Enter to win a $50 gift card to Roundhead Brewing Co. in Hyde Park

Enter to win a personalized plastic tote from Kids 'R' Kids in West Roxbury

Enter to win a Handmade Leather Nantucket Bracelet

$200 Gift Card to Dam MedSpa in Dorchester

Enter to win a chance for your student to decorate cookies or cupcakes with Ms. Scipione & Ms. Veness after school! Two winners can pick two friends each to join them in cookie or cupcake decorating.

Two winners can pick two friends each to have lunch and make slime with Ms. Kopcso and Ms. Petitt at the Kilmer Lower School.

Calling all future leaders!  Has your child ever wondered what it would be like to be in charge of an entire school? One lucky student will get a chance to be Principal of the Kilmer Upper School for the day!  

Calling all future leaders!  Has your child ever wondered what it would be like to be in charge of an entire school? One lucky student will get a chance to be Principal of the Kilmer Lower School for the day!  

One winner can pick two friends each to play Mario Kart with Mr. Mendez at the Kilmer Upper School during lunch/recess

One winner can pick two friends each to play Mario Kart with Mr. Mendez at the Kilmer Lower School during lunch/recess

Enter for a chance for your child to take over Ms. Jackie's desk and be secretary for a day at the Kilmer Lower School!