Discovering White Plains, New York: A 2-Day Itinerary

Hello again, fellow travelers! (And if you’re here for the first time, a big welcome to you!) As many of you know, this year’s adventure is all about rediscovering the USA. I’ve been chronicling my journey to visit all 50 states during my 60th year over on 50 at 60, and let me tell you, it’s been a whirlwind of sights, stories, and experiences I wouldn’t trade for anything.

Right now, I’m prepping for season #5, and I’m looking forward to bringing something new to the table. I’ll be interviewing creatives and entrepreneurs I meet along the way, shining a light on their unique perspectives and the fascinating work they’re doing. It’s been a great learning curve, and I’m soaking up every moment—and having so much fun in the process!

These posts are a sneak peek into the pre-planning phase of what’s to come. With a little AI help, I’m mapping out routes, brainstorming ideas, and setting the stage for future travels. It’s all about finding that sweet spot between well-planned journeys and the magic of the unexpected. The road ahead looks promising, and I’m excited to see where it leads.

So, hang tight—more updates and insights are on their way as I gear up for the next leg of this adventure!


White Plains, NY

Situated in the heart of Westchester County, White Plains is a dynamic city known for its vibrant downtown, historic charm, and diverse cultural attractions. As a key suburban hub just north of New York City, White Plains offers a blend of urban convenience and local charm, making it an excellent destination for a quick getaway. This two-day itinerary will guide you through the best of White Plains, from exploring its historic sites and scenic parks to enjoying local dining and discovering unique artistic offerings. Get ready to explore this charming city with a mix of history, culture, and relaxation.

Day 1: Arrival and Evening Exploration

  • Arrival and Check-In: Arrive in White Plains by late afternoon and check into a comfortable accommodation like The Ritz-Carlton New York, Westchester, offering luxurious rooms and top-notch amenities, or Hyatt House White Plains, known for its modern comfort and convenient location.
  • Evening Stroll: After checking in, take a relaxing walk through White Plains’ downtown area, where you can explore the lively streets, enjoy the local shops, and soak in the city’s atmosphere.
  • Dinner: Dine at The Melting Pot, an upscale fondue restaurant offering a unique dining experience with a range of delicious options for every taste. It’s a fun and interactive way to enjoy your meal.

Day 2: Exploring White Plains

  • Breakfast: Start your day with breakfast at Dough Nation, a local favorite known for its delicious donuts and coffee in a casual, friendly setting.
  • Morning Exploration: Visit Kykuit, the Rockefeller Estate, located just a short drive from White Plains in Pocantico Hills. This historic estate offers guided tours of the grand mansion, beautifully landscaped gardens, and impressive art collections, providing a glimpse into the grandeur of the Rockefeller family.
  • Lunch: Enjoy a casual lunch at The Brass Rail, offering classic American fare and a cozy atmosphere. It’s a great spot to relax and enjoy a hearty meal.
  • Scenic Drive: Take a scenic drive through Recreational Park and Tarrytown, exploring the picturesque Hudson River views and charming small towns. This drive provides excellent opportunities for photos and a peaceful escape from the city.
  • Afternoon Activity: Explore the White Plains Historical Society, which offers exhibits and information about the city’s history and heritage. It’s a great way to learn more about White Plains and its historical significance.
  • Dinner: For dinner, try The Cookery, known for its creative Italian dishes and a welcoming, relaxed atmosphere. It’s a fantastic place to end your day with a delicious meal.

Day 3: Morning Farewell

  • Breakfast: If time permits, enjoy a final breakfast at The Breakfast Club, offering a variety of tasty breakfast options and a charming atmosphere.
  • Morning Stroll: Take one last walk through Bryant Park, a lovely green space where you can relax and enjoy the tranquil surroundings before you head out.

As your visit to White Plains concludes, consider taking a short drive to explore Scarsdale, a nearby town known for its charming architecture, scenic beauty, and upscale shops. It’s a delightful way to extend your exploration and experience more of the elegance and charm of Westchester County before heading home.

“This post, it’s itineraries, and the accompanying artistic images were crafted with the assistance of AI technology, blending human creativity with artificial intelligence to explore new possibilities in travel and visual storytelling. While these images evoke the essence of their real-world counterparts, they are the result of artistic imagination, designed to transport you to places both familiar and fantastical. For a deeper understanding of our use of AI in creating these elements and its implications, please refer to our comprehensive AI statement linked here.”