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Transitional fall activities are a great way to wind down the big summer buzz and rejuvenate once the kids go back to school. This is the time to still enjoy outdoor events before the pumpkins and hayrides show up. The weather is not mid-July hot, but still not cold enough to bring out even your trench coat. If you want to spend time outside of the city there is a lot here for you to do, including day-trips upstate or a drive to the Hamptons.

1. Explore the Whitney Museum:

The Whitney Museum is slowing becoming one of my favorite museums in New York City. There’s a large collection of art ranging from the early 1900’s to art reflecting the state of New York in 2020. Below is a beautiful piece by Georgia O’Keeffe, Music, Pink and Blue No. 2 (1918), oil on canvas. This one stuck out to me as I walked through the museum. Even with my MoMa membership, I felt the money spent here was well worth it for what I came away with. Visiting the Whitney will give you a sense of understanding and connection to the American experience over the past 100 years.

Georgia O'Keeffe, Music, Pink and Blue No. 2 (1918), oil on canvas.

2. Visit the Little Island

The Little Island, which is not far from the Whitney, is a floating park with views of the city. Although you can get there making your way across the busy Westside highway, once there you are among trees and beautiful foliage that take you away from the hustle and the bustle of the city if only for a few hours. And the best part, its free.

3. Head to the Hamptons for Wine Tasting:

The Hamptons during the summer can be overwhelmingly busy. Traffic backed up for hours. Believe me the Hamptons in September will still have you questioning what other routes are available for getting there. But, if you head out early you can avoid the congestion and end up in a tranquil piece of New York, you never knew existed. Leaving the beaches of the Hamptons behind, September is a lovely time for wine tasting. There are a variety of vineyards that will peak your interests, I recommend trying Wolffer Estate for a lovely day out.

4. Get a Facial at Savor Beauty Spa

Savor Beauty Spa has been my go-to place for facials for the past year. There is something so soothing and relaxing about walking in there and feeling like a queen for the afternoon. The service is impeccable and the champagne facial is one I could do over and over again. Interested in an afternoon of luxury? Click here for more information.

5. Get Dressed Up for the New York Renaissance Faire

One of my new favorite fall activities most certainly has to be dressing up for the New York Renaissance Faire. There’s so much to do whether your kid or a big kid. From the food to the jousting, it’s like bringing all of Renaissance England to life. Heading to the Renaissance Faire remember to bring cash, not many vendors accept cards (ATMS available). It is also best to purchase tickets ahead. My best advice is to arrive early, even when you get to Tuxedo Park, the line for parking can be 30 to 45 minutes.

6. Enjoy a Fall Picnic in Central Park

Fall activities in New York City would not be complete without a picnic in the park. Central Park will always be the place where I bring my blanket and picnic basket for a relaxed picnic when the weather is still comfortable. Whether you’re near the water, or the numerous footbridges remember to clean up after yourselves when it’s time to leave.

7. Take a Day Trip to Montauk

Looking for a day trip outside of the city, head to Montauk. There’s still much to do and see in September. The weather is perfect for long walks and you will need them after stopping at some famous lobster and oyster shacks. Even though summer is long behind us, people are still heading to Montauk. Leave early to avoid traffic. Once there find some parking and enjoy the scenery. If you are heading to the lighthouse remember to hold on to your hat for those windy walks.

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