One student and a friend will grab a slice at lunch with Dalton's very own Head of School José M. De Jesús.

You and your guest will receive 2 VIP Tickets to "The Late Show with Stephen Colbert." The Late Show tapes Mondays through Thursdays. The arrival time for VIP audience members is 3:30-4:00 p.m. SHARP at the world-famous Ed Sullivan Theater. The show will tape from 5:30-7:30 p.m.

Two hard-to-get tickets to Saturday Night Live can be yours! Don't miss your chance to experience this iconic NYC show in person in May at the legendary studio 8H at 30 Rock.

See the one-and-only Dua Lipa, the Grammy award-winning pop sensation, at Madison Square Gardens on September 20, 2025 at 7:30 PM. This prize includes 4 tickets - exclusive box seats in the luxe Tao's Suite Sixteen, featuring leather stadium-style seating with a prime view of the arena floor.

Private wine tasting and dining experience at the award-winning Temperance Wine Bar in the West Village. Enjoy a 2-hour curated interactive and educational wine tasting and food pairing for up to 16 individuals. This can be hosted on any day except Mondays and holidays.

Rolling Stone calls Brooklyn Bowl, "one of the most incredible places on earth!" With world-class music, food, and bowling, we couldn't agree more. The winner will receive four (4) tickets to any show (even sold-out shows) at the NYC location.

Swish! The winner of this prize will receive tuition for one (1) fall session Dribbl. Dribbl is an instructional and recreational basketball program for children from preschool through 8th grade, offering weekend classes at locations throughout NYC and Brooklyn. For 30 years, Dribbl has stood out as a fun, recreational program for young athletes who want to learn fundamental basketball skills in a positive and supportive environment.

Calling all future ice skating stars: This package includes three lessons, one hour each, with Coach Wendy Wilke P'37 at Chelsea Piers (ice time and skates not included). After participating in many world tours, Wendy has been a figure skating coach coast to coast for 30 years. This package can be used any time of year (no expiration date).

Sail the Hudson with an experienced captain, Glen Popick (P '20, '24, '27). Enjoy a two-hour sunset cruise for up to four passengers in NYC. Date and time to be mutually arranged.

This prize includes a two-night stay in a Luxury Suite in The Palazzo at The Venetian Resort in Las Vegas. You'll also receive a $500 food & beverage credit at participating restaurants at The Venetian; 2 tickets to see the extraordinary illusionist SHIN LIM ("The #1 sleight-of-hand artist in the world," Huffington Post); The Venetian Resort gift basket in suite at check-in, including a certificate for a private Gondola Ride for two.

Yearning for a luxurious stay-cation? Get away from it all without going far. The winner will spend two nights at The Mark Hotel. You'll stay in a Seventy-Seven King guestroom with a breakfast credit of $45 per person included (maximum two people per room).

Your foursome (you, two friends, and the Club member) will enjoy a round of golf plus lunch at the Friar's Head Golf Club. Friar's Head, located on the East End of Long Island, is ranked as one of the top 20 golf courses in the country. Redeemable any time during the week, or a late morning or afternoon tee-off on a weekend.

Host a lively party for your child at the Dalton gym with lots of room to run around in fun games led by two coaches. This prize Includes use of the gym facility and two coaches.

Ever wonder what it takes to create Connections, the New York Times word puzzle which delights and confounds so many of us? This lucky winner will spend a few hours with Connections Editor Dalton Alumna Wyna Liu '01 in an "Ask Me Anything" session. Wyna will "pull the curtain back" and explain what goes into creating Connections and will answer your questions about puzzle-making!

See the LA Dodgers, World Series Champs, and superstar Pitcher Shohei Ohtani play at home in Los Angeles. This amazing package includes 4 tickets, dugout seats, food, VIP parking, and batting practice!

Two tickets to see the Tony & Academy Award winner Denzel Washington star as Othello, the noble Moor of Venice and commanding warrior-general. Opposite him, Tony & Academy Award nominee Jake Gyllenhaal portrays Iago, the ambitious lieutenant and masterful manipulator. Tickets are for Wednesday, April 23 @ 7:00 PM.

Two tickets to see Just In Time, an exhilarating new musical that will transport audiences into an intimate, swinging nightclub complete with a live band, a stellar ensemble cast, and iconic Bobby Darin hits including "Beyond the Sea," "Mack the Knife," "Splish Splash," and "Dream Lover." Discover the man behind the music - a once-in-a-lifetime talent who knew his time was limited and was determined to make a splash before it was too late. Broadway Legend Jonathan Groff plays Bobby Darin and Dalton Alumna Gracie Lawrence '15 plays Connie Francis!

Date of show: Wednesday, April 30 @ 8:00 PM

Two tickets for Tuesday, April 29th @ 7:00 PM to see the Emmy Award winner Sarah Snook, star of HBO's smash-hit "Succession," reprise her Olivier Award-winning performance in The Picture of Dorian Gray on Broadway. In an acting coup for the ages, Snook takes on all 26 roles in this gripping, witty and vibrantly contemporary production that breathes new life into Oscar Wilde's classic tale.

Delish! A dining experience for 2 at the renowned Blue Hill New York's Family Meal - a fun, menuless dinner experience of shared plates. Blue Hill New York sources ingredients from Blue Hill Farm, Dalton Alum and Chef Dan Barber's family dairy in Great Barrington, Massachusetts; from the Stone Barns Center for Agriculture in Pocantico Hills, NY; and from farms within 250 miles of New York City.

Elevate your style with a luxurious addition to your Dalton wardrobe - the Caltori Tolliver Tiger Hoops in solid 14K gold earrings. These exquisite hoops with Tiger charms are crafted from 100% recycled, ethically sourced gold certified by the Responsible Jewellery Council (RJC). Hoop dimensions: 12mm x 1.3mm (interior diameter: 10mm), Post length: 5mm, Charm size: 8mm x 13mm x 4mm

Calling all Andy Cohen fans! How about a voucher for (2) tickets to a taping of Watch What Happens Live with Andy Cohen in New York City? Restrictions: Unfortunately this does not include a meet and greet or a photo with Andy. Tickets are subject to availability and programming. Guests on the show are subject to change at any time and may not be predetermined at the time of booking.

Please note that tickets must be booked in advance and the winner and guest must be over the age of 21 to attend. Tapings are also subject to change at any time and expire one year from the purchase date & cannot be combined with other pairs of WWHL tickets.

Pirate's Oak is Southern island living at its finest! If you're searching for the perfect Hilton Head vacation house, this stunning home has everything you need for an unforgettable getaway. Featuring 7 bedrooms, 5 full bathrooms, and 2 half bathrooms, it comfortably welcomes up to 18 guests. Located in the exclusive, award-winning Palmetto Dunes Resort, this 2,000-acre beachfront community offers three miles of Atlantic Ocean coastline, miles of bike paths, three world-class golf courses, an award-winning tennis center, and an 11-mile lagoon perfect for kayaking, fishing, and exploring. With nearby restaurants, shopping, and attractions, it's the ultimate Hilton Head vacation rental spot.

Thursday-Sunday winter getaway Dec-March Excluding Spring break and holidays

Spend an unforgettable week in Paris ensconced in a beautiful family apartment with 3 bedrooms, 2.5 bathrooms, a full kitchen, and a separate study/library. A washer and dryer and Wi-Fi are available. Ideally situated in the Left Bank of Paris (6th Arrondissement), the apartment is located at the corner of Place St. Sulpice, close to the Luxembourg Gardens and Boulevard St Germain. It's an easy walk to the Seine, Le Louvre, Musee d'Orsay, Eiffel Tower, and Cathedral Notre Dame. Dates to be arranged with the host (Dalton Parent).

No pets, sleeps up to 6 people, Dalton affiliated families and friends only.

You and three guests will have prime seats to the world-famous Macy's Thanksgiving Day Parade! This American tradition features innovative floats with performers, larger-than-life balloons, the nation's best high school and college marching bands, and the one-and-and only Santa Claus for the best Thanksgiving Day ever!