@jsgmom Thanks for reaching out and welcome to the community!
We're going to tag some of our users from in and around New York to see if they have some suggestions for you!
Hey there @jsgmom if you’re up for trying something different, I’ve heard great things about The Giant Stairs Hike in the Palisades. It is at the state line lookout exit on the Palisades Parkway. I haven’t been there yet but I hear that it rarely gets busy and is a unique challenge!
@jsgmom Check out Breakneck Ridge located near Cold Spring, NY. Along the Hudson. You can actually take Metro North from Grand Central and walk about ten minutes from the train to the trailhead.
Speaking of Metro North you can also take it to Appalachian Trail Station, (on Saturdays and Sundays) and get right on the AT.
One more, Fahnstock State Park, about 75 minutes north of Manhattan, off the Taconic State Parkway. Great hiking, and the AT passes through there also.
Sorry if this is way too late to be useful, but the Greenbelt in Staten Island is probably your best bet at a great day of hiking and a fun day trip in the NYC area. If you've never been to SI, hear me out. Visitors from elsewhere in the city:
-Start their day with a half hour boat ride, with the Statue of Liberty on one side and the sun rising over Brooklyn/the Pacific Ocean on the other.
-have access to over 30 miles of trails, which you can access almost as soon as you step off the boat! (it's possible to walk through/alongside parkland for the ~4 or so miles from the boat to the Greenbelt)
-can visit forests, meadows, swamps, beaches, and the tallest natural points on the eastern seaboard - all within a 12 mile hike!
-end their day in the borough of NYC with the most small restaurants. Thai, Mexican, Chinese, Sri Lankan, North African, Italian, whatever you want, you can find it on SI nearby a green space or on your way to/from the ferry!
I'm more than willing to talk about specifics, let me know if you're still reading these replies and if you are considering a trip to our fine Island.
My recommendation is not in the NYC area but if you do not mind heading over to New Jersey about 1.5 hour drive south... you can get to this amazing and peaceful camping at Belleplain State Forest. Plan a weekend with one of the 169 tents that you can rent out or just just pay per day for camp sites! You can go swimming on the north side of Lake Nummy (a former cranberry bog transformed into a 26-acre recreational lake), where lifeguards are on duty from Memorial Day Weekend (almost fully booked this year so hurry up) through Labor Day Weekend. Or take your pick from other recreational activities; boating, hiking, horseback riding, fishing and mountain biking are all options at a surprisingly low price.
If you prefer to stay up north with the cold, then I highly recommend going to High Point State Park. You can reserve one of the 50 campsites (no tent rent service) at this forested state park for a somewhat peaceful getaway (alot of bear activity so be careful) in the woods. I think you can still swim at the spring-fed Lake Marcia, or launch a boat at Sawmill Lake or Steenykill Lake. While you’re there, be sure to climb to the top of the 220-foot High Point Monument for sweeping vistas of the Pocono and Catskill mountains! Definitely instagram worth content.
P.S. I'd love to go to Bear Mountain but it have been fully booked since late January :'(
Hope that helps
My favorite spots for short hikes, and a couple for longer:
1. Mt Holly Sanctuary (Nature Conservancy) and Yarrow Preserve (adjacent to each other). Probably doing all trails in both can be a nice long hike. Westchester County, near Katonah. Edit to add: also the Zofnass Family Preserve and the adjacent preserve together have a good 10+ miles of trails. Also in that general area!
2. Hardscrabble Wilderness near Pleasantville. Park per Google maps. Not a long hike but longer if you try doing all the trails. For nearby or long flat hikes the OCATT!
3. Lots of trails near the Hudson near Haverstraw. I parked on the opposite side of Rt 9 and crossed over to avoid crowds.
4. In NJ not far: Osio Overlook. Parking gets busy though, especially weekends. Very hilly!
5. Stewart State Forest for flatter trails but lots of them!
6. Bigger longer hikes in Harriman on the Island Pond side which is partly Appalachian Trail. I park here: https://goo.gl/maps/DhiKQXH2PGDSU7Xi8
A good way to find hikes is to join Geocaching, there are a lot of caches set for circular hikes all over the tri-state area. That brought me to the beautiful Saugatuck Trail out near Westport CT which I loved.