Here's What's Happening At Bosse In Natick This Month

NATICK, MA — The weather may be getting warmer, but the dreary, rainy New England days are sure to come this spring.

Enter Bosse, the Natick pickleball and restaurant complex with a lengthy schedule of events for the month of May.

Some events are already ongoing, but Bosse sent us a longlist of their efforts this May. Here's what to know:

Celtics Playoff Nights

Every Celtics Playoff Game | Sports Lounge

$1 wings all day long every Celtics playoff gameday. Whether you’re chasing banners or just chasing flavor, Bosse’s Sports Lounge is the ultimate watch party destination.

More Info

Pickleball Leagues

Starting May 4 | All Skill Levels

Weekly match play, updated standings, and plenty of on- and off-court community. Sign up solo or with a partner.

Join now

Mother’s Day: Pinkleball Presented by Whispering Angel

Saturday, May 10 | 3–5 PM | Pickleball Courts

Celebrate in style with flowing rosé, elevated small bites, and social ladder play. Perfect for beginners and intermediates. $50 non-members | $45 members.

Sign up here

Mother’s Day Brunch at Enoteca

Sunday, May 11 | Enoteca

A festive brunch featuring indulgent seasonal dishes like Bananas Foster French Toast and Carbonara Pizza. Kids’ menu available.

Reservations

Pickle Party: Ladder Play, Fried Pickles & All the Vibes

Friday, May 16 | 6:30 pm – 8:30pm

Organized round robin play for 2.5–3.5 level players with fried pickles, drinks, and music to match the mood. Come to ready to play, stay for the energy, and leave with new friends and bragging rights. $40 non-members | $35 members.

Sign up here

Bosse Signature Series Featuring Will Howells

May 17–18 | Pickleball Courts

Train with @officialapptour World #1 and APP Triple Crown winner Will Howells in this weekend clinic series packed with coaching, strategy, and hands-on instruction from one of pickleball’s fastest-rising talents.

Register

Dinks & Drinks: A Men’s Pickleball Social

Thursday, May 22 | 6:30pm – 8:30pm

This men’s-only evening is for players in the 3.0–3.9 range looking for a little friendly competition and a whole lot of fun. $40 non-members | $35 members.

Sign up here

Meet Your Match: A Pickleball Singles Social

Friday, May 23 | 6:30pm - 8:30pm

This special singles event mixes the fun of rotational play with a light competitive edge. Players will rotate partners and opponents throughout, with King/Queen of the Court rules to keep things moving and keep the chemistry following. For singles aged 21-35. $40 non-members | $35 members.

Sign up here

Sweets & Treats: A Pickleball Social

Tuesday, May 27 | 9:00am – 11:00am

Drop in for morning play and pastries with fellow 3.0–3.9 players. Coffee, treats, and top-notch rallies await. $30 non-members | $25 members.

Sign up here

Pickleball for a Purpose with Rob Gronkowski

Wednesday, May 28 | 5–8 PM | Pickleball Courts

NFL icon Rob Gronkowski brings his signature energy to Bosse for a special night of fundraising and fun. The top fundraising teams—plus one wildcard—will earn the chance to play pickleball with Gronk and friends, all in support of Dana-Farber Cancer Institute and the Gronk Nation Youth Foundation.

Fans can participate as players or spectators, with prize tiers offering signed Gronk gear and VIP experiences.

Register or donate

Paddles & Prosecco: A Women’s Pickleball Social

Thursday, May 29 | 6:30pm – 8:30pm

Raise a glass and your game during a laid-back evening of organized open play, perfectly paired with Prosecco, small bites, and great company. Designed for women playing at the 2.5-3.5 level. $40 non-members | $35 members.

Sign up here

Bosse Tournament Series

May 31 – June 1 | Pickleball Courts

The Bosse Tournament Series features round robin competition, playoff pressure, and brag-worthy prizes, all in an atmosphere that brings the energy every time. DUPR scores count.

Register