NYC Life: Escapes, Cabaret, Shakespeare, Harlem and More

Photo: Nicole Freezer Rubens

Let the good times pour. Grab your spot for our annual wine trip to the North Fork of Long Island. August is anything but idle in NYC. Harlem Week and Shakespeare in the Park are back. There’s a fun and nostalgic cabaret show at Don’t Tell Mama and Hudson Yards is rolling out the red carpet for our four-legged friends. Our Long Island reporter changes her focus this week from great things to do to women who are doing great things. Our roving photographer takes us to Mont-Tremblant this week.

Join Us for a Wine Lover’s Escape – Sunday, Sept 14!

We’re heading to the beautiful North Fork of Long Island for a fabulous day of wine, music, and fun! Your ticket includes round-trip transportation (from NYC or Hicksville), visits to three vineyards, wine tastings, a picnic lunch, live music, and gift bags—plus surprise bus prizes and a lively crew of wine-loving “tomatoes” (yes, guys are welcome too!). Sip, savor, and celebrate with us—space is limited! GET THE DETAILS.

Aug. 15. Michelle DellaFave—Dean Martin’s Golddigger—Returns to the Spotlight

No, you’re not seeing things—that is Dean Martin, and yes, that’s Michelle DellaFave, one of his original “Golddiggers,” taking center stage once again. On Friday, August 15 at 7PM, DellaFave brings her radiant presence and rich vocal stylings to Don’t Tell Mama in Manhattan with her new show, “Diggin’ Life.”

A beloved face from the 1960s, Michelle DellaFave rose to fame as one of “The Golddiggers” on The Dean Martin Show, later performing as part of “The Dingaling Sisters” and starring in their own summer series. Her career includes collaborations with legends like Frank Sinatra, Bing Crosby, Lena Horne, and Bob Hope—whom she joined on multiple USO tours, including two in Vietnam. She’s also graced The Tonight Show Starring Johnny Carson and The Mike Douglas Show.

Directed by Tanya Moberly, “Diggin’ Life” features a vibrant mix from the Great American Songbook, with selections by Johnny Burke & Jimmy Van Heusen, Francesca Blumenthal, Jerome Kern, Leon Russell, and more. DellaFave will be joined by Ian Herman on piano and Ritt Henn on bass, promising a night of timeless melodies and heartfelt interpretations.

Reservations are highly recommended at donttellmamanyc.com. Tickets are $35, with a $20 per person minimum (including two drinks). Don’t Tell Mama offers a food menu and operates as a cash-only room.

Aug. 1-17. Harlem Week 2025: “Celebrate Our Magic”

This year’s Harlem Week honors the neighborhood’s rich legacy and the visionary leadership of co-founder Lloyd Williams, who passed away at 80. As one of NYC’s largest cultural festivals, it draws nearly 2 million visitors for two weeks of music, dialogue, wellness, and celebration.

 Festival Highlights

🎶 Music & Culture

  • Harlem Summerstage (Aug 9): Global and local performances
  • A Great Day in Harlem (Aug 6): Musical heritage showcase
  • Uptown Night Market (Aug 7 & 14): DJs, food, and 50+ vendors

 Community & Conversations

  • Harlem On My Mind (Aug 5, 12, 13): Panels on culture and youth
  • Climate Change Conference (Aug 6): Urban sustainability focus

 Wellness & Family Fun

  • Percy Sutton 5K Run (Aug 6)
  • Children’s Festival (Aug 6 & 16): Games, spelling bee, activities
  • Senior Citizens Day (Aug 1): Music and wellness tributes

 Careers & Youth Empowerment

  • Jobs & Career Fair: Workshops and networking
  • Youth Conference (Aug 7): Leadership and development

 Street Festivals

  • Summer Streets (Aug 2, 9, 16): Car-free zones with pop-ups
  • Harlem Day (Aug 17): Grand finale with films and cultural showcases

GET THE DETAILS.

Now- Sept. 14. Shakespeare in the Park 2025: Twelfth Night at the Delacorte Theater

After a two-year renovation, Central Park’s iconic Delacorte Theater triumphantly reopens with a star-studded production of Twelfth Night, . Directed by Saheem Ali, this joyful comedy of mistaken identities and love triangles features an extraordinary cast: Lupita Nyong’o, Sandra Oh, Peter Dinklage, Jesse Tyler Ferguson, and Junior Nyong’o as the shipwrecked twins Viola and Sebastian.

 A Revitalized Theater Experience

The $85 million makeover includes:

  • Sustainable façade made from reclaimed NYC water towers
  • Wider, more comfortable seating (1,866 total, with 34 ADA-accessible spots)
  • Upgraded lighting, dressing rooms, and flood protection
  • Enhanced accessibility with ramps, lifts, and new entry gates

 How to Get Free Tickets

Tickets are free, in keeping with founder Joe Papp’s vision of “Free. For All. Forever.” Here’s how to snag a seat:

  • In-person distribution at the Delacorte Theater (line starts at 6 a.m., tickets at noon)
  • Digital lottery via the TodayTix app
  • Borough distribution at select NYC locations (vouchers redeemable at the theater)
  • Standby line begins at 6 p.m. for any unclaimed tickets

GET THE DETAILS.




From Gardens to Giggles

Our Long Island reporter switches her focus this week to Long Island women who are creating exciting second acts. On Long Island’s East End, where dunes meet dreams, Madelyn Simon has found her second act tucked among the leaves of her watercolor-painted pages. Retired from a flourishing landscaping career, she pivoted into children’s literature, crafting vibrant tales that sing the praises of friendship, curiosity, and the natural world. READ MORE.

Paw Play Days: Leash Up Your Pup

Hudson Yards is rolling out the red carpet for four-legged friends with its lively summer series, Paw Play Days. Held monthly through October in the Public Square & Gardens, these free events are part of the Backyard at Hudson Yards programming presented by Wells Fargo. It’s a joyful celebration of NYC’s pet-loving community, offering treats, portraits, and plenty of tail wags in one of Manhattan’s most stylish outdoor spaces.

Visitors can enjoy complimentary dog portraits and snacks courtesy of Dog City, while mingling with adoptable pups from Rescue City and Animal Haven. Dylan’s Candy Bar’s nonprofit also joins the fun with pop-ups supporting animal welfare causes. Shake Shack on Level 4 is a popular stop for pet-friendly bites, and themed giveaways add an extra layer of delight for both pets and their humans.

Whether you’re a longtime dog owner or just looking to soak up the playful energy, Paw Play Days offers a warm, welcoming space to connect with fellow animal lovers. Admission is free and open to the public, with activities available while supplies last. It’s a perfect excuse to leash up your pup and head to Hudson Yards for a day of furry fun. GET THE DETAILS.

Roving in Quebec

Our roving photographer, Nicole Freezer Rubens writes:

Last weekend to kick off my annual vacation at our summer cottage in Quebec, I spent one night visiting Mont-Tremblant in the Laurentians. Best known as a ski resort in the winter it was surely hopping with summer outdoor lakeside and mountainside activities. The name originates from the Algonquins who called it the “trembling mountain.” Today one can hike to find a multitude of serene waterfalls and spectacular views of the colorful village.

My favorite part of the area was the charming town of Saint-Jovite, named after the simple wooden church still standing today. It’s quaint streets and shops screamed of small town with farmer’s markets, jazz festivals and cute boutiques and restaurants. One could even go on safari at the adorable mini golf course at the edge of town. This was a perfect gateway into my back to basics retreat from big city life. Please stay tuned for more rest and relaxation photos next week.

~Nicole Freezer Rubens is the author of “The Long Pause and the Short Breath”

The tomato behind The Three Tomatoes.
Cheryl Benton, aka the “head tomato” is founder and publisher of The Three Tomatoes, a digital lifestyle magazine for “women who aren’t kids”. Having lived and worked for many years in New York City, the land of size zero twenty-somethings, she was truly starting to feel like an invisible woman. She created The Three Tomatoes just for the fun of it as the antidote for invisibility and sent it to 60 friends. Today she has thousands of friends and is chief cheerleader for smart, savvy women who want to live their lives fully at every age and every stage. She is the author of the novel, "Can You See Us Now?" and co-author of a humorous books of quips, "Martini Wisdom." Because she's lived a long time, her full bio won't fit here. If you want the "blah, blah, blah", read more. www.thethreetomatoes.com/about-the-head-tomato

Cheryl Benton

The tomato behind The Three Tomatoes. Cheryl Benton, aka the “head tomato” is founder and publisher of The Three Tomatoes, a digital lifestyle magazine for “women who aren’t kids”. Having lived and worked for many years in New York City, the land of size zero twenty-somethings, she was truly starting to feel like an invisible woman. She created The Three Tomatoes just for the fun of it as the antidote for invisibility and sent it to 60 friends. Today she has thousands of friends and is chief cheerleader for smart, savvy women who want to live their lives fully at every age and every stage. She is the author of the novel, "Can You See Us Now?" and co-author of a humorous books of quips, "Martini Wisdom." Because she's lived a long time, her full bio won't fit here. If you want the "blah, blah, blah", read more. www.thethreetomatoes.com/about-the-head-tomato

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