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I’m a graduate student and father of a 4-year old living in NYC. This has necessitated lowering my ambition to bag peaks. Luckily, my little boy loves being outdoors and can hike up to 3 miles at a time and 6 miles in one day given enough time. He has completed the listed hikes below either under his own power, on my back, in my arms, or most likely a combination of all three (and in a few cases in his Mom’s belly). In the foreseeable future I have the modest goals of completing the hikes in the following guidebooks with my family:

60 hikes within 60 miles, Christopher and Catherine Brooks, NY-NJ Trail Conference
Day Walker, 32 Hikes in the New York Metropolitan Area, American Hiking Society

Below is information for my record keeping, but if you’re interested - enjoy.

Best NYC hikes with toddlers:

1) Fire Island (Sayville, NY) - easy
1.5 miles of boardwalks that meander through an old growth forest plus an uncrowded white sand beach - my 3 year old's version of paradise.

2) What I am calling the New Jersey "Swampies". All three areas (ranked below) are great for 2 - 5 year olds. Within you will find boardwalks, bridges, ramps, boardwalks, birds, blinds, boardwalks - did I mention the boardwalks?
A. Cheesequake (Matawan, NJ) – moderate
B. Great Swamp Wilderness Trail (Summit, NJ) – easy
C. Shark River Circuit (Neptune, NJ) – easy

3) Hook Mountain (Nyack) - difficult
4) Storm King (Cornwall) – very difficult
5) Clay Pits Connector (Staten Island) - easy
6) Teatown Triple (Ossining) - easy

Total unique NYC hikes: 64
Total NYC hikes: 75

60 hikes within 60 miles, Christopher and Catherine Brooks, NY-NJ Trail Conference, 2nd + 3rd Editions
<43/68 complete – 63%>

2 - Anthony's Nose
Winter (2016), good hike which we started from Trail Side Museum (North) differing from guidebook instructions. This allowed us to visit the small zoo, cross Bear Bridge, and then hike up the short but steep trail to Anthony's Nose. This allowed many views of metro north trains - my son approved.
3 - Butler Outer loop trail
Winter (2015), mediocre hike which we did with 24+ inches of compacted snow on ground. Route we choose had limited views (except Hawk point) and lacked areas of interest … but we had fun playing in the snow.
7 - Fishkill Ridge Trail
Fall (2013), excellent hike with very good views especially during the traverse from Lambs Hill to Bald Hill. Unfort. the hike is too hard to be enjoyable with kids – at least mine.
8 – Hudson Highlands Breakneck Ridge Loop
Summer (2010), excellent hike and easy scramble with good views during the initial climb up breakneck ridge. My wife was pregnant but as usual that didn’t slow her down. This trip would be very hard for kids but I know my 4 year old now would love the scrambling.
9 - Mianus River Gorge Trail
Fall (2013), good hike with good views of the gorge and S.J. Barge Reservoir. There was plenty of interesting obstacles, mini scrambles, and areas of interest for kids.
10 – Pelham Bay Island Loops
Summer (2012), very good hike with some great views of the Long Island Sound. Great for kids with many rocks, boardwalks, and beaches for play. However area lacks any wilderness feel and is crowed (found discarded dime bags of various drugs in large numbers just slightly off trail).
11 - Rockefeller Medley
Fall (2015), good hike with beautiful scenery around Swan Lake. Hiking in the hills on the Eastern end of the park yielded okay but not spectacular views. Great for kids with many birds to watch, bridges to cross, and rocks to throw into ponds.
12 – Teatown Triple
Winter (2013), (snow on ground/lake frozen), great hike with good views of the lake and the surrounding hills. Many boardwalks over marshy and lake areas that held my son’s interest.
13 - Ward Pound Ridge Star Loop
Fall (2015), good hike with great fall colors that toured the Cross River and Deer Hollow (valley between rollings hills). There were playgrounds for kids in several areas as well as several boardwalks around the river.
14 – Westchester Wilderness Walk
Summer (2012), mediocre hike with views of forest and some minor wetlands. There were some obstacles that my son enjoyed but overall lacked points of interest.
19 - Harriman Highland Trails
Spring (2014), great hike with views that span the highlands. Difficult for children at first but once you reach the plateau there are many scrambling opportunities including the lemon squeezer.
20 - Harriman Seven Hills Loop
Spring (2012), okay hike which spans several regions of Harriman, not enough points to keep my son's interest, would return to do southern portion
21 - Hook Mountain
Fall (2013), excellent hike with great views of the Hudson and Tappan Zee Bridge. We saw many eagles, hawks, and other birds at the summit. The hike was difficult but worth it with kids.
22 – Schunemunk Mountain Ridge Loop
Summer(2011), great hike with great views of Rockland/Orange county including the distant Catskills once the plateau was gained. A highlight was the monoliths found near the summit area. My wife was pregnant and handled the hike fine but it is probably too difficult for most kids
23 – Storm King Summit Trail
Fall (2012), awesome hike with great views of Hudson Highland (+ Black Forest) regions – the best views are from Butter Hill. We saw several eagles/hawks along the way. The trip was very difficult with/for my son but was worth it - one of the best hikes in close proximity to NYC.
24 – Tors Thunder Tour
Fall, (2009) great hike with views of the Hudson River in the Yonkers regions. Good wildlife opportunities as we saw a family of white-tailed deer plus there are a few easy scrambles for kids to enjoy.
25 - Caleb Smith Full Circuit
Winter (2015). Okay hike with views of a small lakes and open fields which we did with 3-4 inches of snow on the ground. This made it more interesting with some snow activities but in generally there is a lack of interesting areas.
26 - Caumsett Neck Loop
Summer (2014), good hike with views of Long Island Sound and CT. Excellent for kids as there are a couple old buildings/farm structures that interested my son. We also went swimming at beach with zero other people there – a rare feat in NYC area.
27 – Clay Pit Ponds Connector
Late Fall (2014), excellent hike for kids (maybe not adults) with many boardwalks and lazy streams to explore.
28 - Connetquot Continuum
Summer (2014), average hike that tours old hunting lodge, several lakes, a river, and the ruins of an old fish hatchery. This area is good for kids with several boardwalks, fishing piers, and meandering water ways the flow around the hatchery.
29 – David Weld Sanctuary Tour
Summer (2014), average hike with good views of the sound, some very steep drop-off you have to be careful of with kids, wouldn’t return
30 – Jamaica Bay West Pond Trail (2X)
Summer (2014), average hike with good views of Jamaica Bay. This area is excellent for children with exceptional animal viewing, notably birds, throughout.
Spring (2015), same as above. Also hiked around East Pond which also had exceptional animal viewing – in this case swans.
31 – Muttontown Mystery Trail (2X)
Spring (2014), average hike with no views. However, it is good for kids with several small lakes/marsh areas and the ruins of King Zog’s estate to explore.
Spring (2015), same as above. Explored King Zog's estate again including the courtyard. My three year old loved that part.
32 – Sunken Meadow to Nissequogue River Trail
Winter (2013), good hike with good views of the sound throughout. There was also boardwalks and hills to explore which my son enjoyed.
33 – Walt Whitman Sampler (Jaynes Peak)
Winter (2013), average hike with no views that tours the high point area of Suffolk county. Although this hike is much more interesting than the drive up to high point (directions @ cohp.org). Good for kids with playground at the start.
36 – High Point Duet
Summer (2013), okay hike with excellent views of North Jersey/Orange County (NY) from the summit highpoint. The southern loop described in the guidebook is okay with limited views of a moderate size lake. The hike (barring the highpoint) isn’t good for kids as there aren’t enough points of interest.
40 - Sterling Ridge Trail
Fall (2015), good hike with views of Sterling Lake and Greenwood lake. The top of the ridge had a closed 6 story fire tower which we climbed anyways.
42 - Turkey-Egypt Connection
Winter (2015), good hike with some view of surrounding area. It was excellent for children as there was good wildlife viewing - saw 6 hunting turkey vulture at Lucy's overlook and several interesting glacial erratics to explore.
44 - Wawayanda 2:Terrance Pond
Spring (2015), average hike with good views of Terrance ponds and valleys between ridges. However, the hike is not great for kids due to difficulty – my son loved all the scrambling but we made slow progress. The first hike my son finally went to the bathroom outdoors – the fear is over.
47 – Cheesequake Natural Area Trail
Winter (2013), excellent hike that explores a wetland area with tons of boardwalks, bridges, and bird viewing opportunities.
48 - Great Swamp Wilderness Trail (2X)
Winter (2014) excellent hike that explores a wetland area with numerous boardwalks and blinds. I recommend the 2 mile boardwalk near the wildlife observation center rather than the trail recommend in the guidebook. Over a dozen bird/turtle viewing which engaged my son for minutes at a time.
Fall (2015) same as above.
50 – Jenny Jump Ghost Lake Loop
Spring (2014), good hike that has views of Ghost Lake and limited views of West Northern Jersey. The lake was still frozen over which my enjoyed throwing rocks onto – however there is lack of interesting areas for children.
51 - Jockey Hollow Run
Spring (2014), average hike that tours historical buildings and rolling hills with no views. Was a good hike for my son as went during raspberry season which keep him well fed and motivated with a new raspberry bush over every hill and around every corner.
53 - Sandy Hook
Summer (2015), used rented bike to tour around the island. We stopped and took a small number of little hikes off the bike trail that went to destinations that included beaches, good views of NYC skyline from North trail, lagoons, and some historical areas. Great for kids.
55 - Watchung Sierra Sample
Spring (2015), okay hike with limited views albeit with an interesting gorge, huge playground for kids, and historical areas.
56 - Babcock Circumference Trail
Spring (2014), okay hike with easy trails for kid but not many sites of interest or worthwhile views. The region is known for its varied flora which was the definitive highlight of the trip.
57 - Bennett's Pond and Beyond
Winter (2016), good hike with some excellent views of the hemlock hills and several wildlife sightings (bird/rodent varienty). My son also had fun with multiple river crossing, bridges, and muddy areas.
60 - Weir Pond and Swamp Loops
Winter (2015), okay hike done with 24+ inches of snow on ground. The snow play was fun but there weren’t enough points of interest beyond the ponds for my son in this small area to warrant another visit.

2nd Edition (removed from 3rd Edition)
1 – Blue Mountain Twin (2X)
Fall (2013), average hike with limited views until Blue Mountain or Mt. Spitzenberg is reached. Need to return to tag summit. Note: Map in the guidebook has significant errors - use site map instead.
Spring (2015), good hike with views of Westchester County, Peekskill area, and the Hudson Highlands in the distance. The trailhead has a great playground and lake area which my son enjoyed immensely.
26 – Great Kills Crooke’s Point Labyrinth
Winter (2014), average hike with good views of NY harbor. There was plenty of beach and water play opportunities for my son.
30 – Uplands Farm Loop
Spring (2013), mediocre hike that tours a retired farm with no views. Okay for kids but the area is quite small and lacks any wilderness feel or points of interest.
34 – High Mountain summit Loop
Spring (2013), good hike with excellent views of NYC’s skyline and eastern jersey’s suburbia. The hike was difficult for my 2 year old son but worth it.
54 - Shark River
Winter (2016), great hike that criss crosses many streams within a wetland. On the trail there are a plethora of boardwalks and bird-watching opps. At the trailhead there was an excellent playground for kids.

Day Walker, 32 Hikes in the New York Metropolitan Area, American Hiking Society
<28/32 complete – 88%>
1 – Alley Pond Park (5X)
Spring/Winter/Fall/Summer (2012-2015), average hike with views of ponds/wetlands on both the North and South divisions of the park. There are also a few large boardwalks on the North side that my son ate up. This was actually the site of his first ever outdoor outing at the age of 9 months – a special memory. Good for kids with a playground on the south trail.
3 - Staten Island Green Belt
Fall (2015), okay hike with no views but some quasi-interesting sites including a ravine and some High Rock Park camp buildings. In close proximity to a carousel, playground and lake area (clogged with swans) that my son enjoyed. May return due to its close proximity to NYC and to explore northern/western areas.
4 – Riverside Park
Summer (2009), good “hike” with views of the Hudson and Grant’s bizarre mausoleum.
5 - Van Cortland Park
Spring (2015), good "hike" with views of the city from a couple vantage places. Recommend path also had a wetland boardwalk and nice playground for kids.
7 - Fire Island - Sunken Forest (2X)
Spring/Summer (2015), excellent hike with 1.5 miles of board walks through the sunken forest and associated wetland areas. Nearby is a relatively empty and pristine beach that is perfect for my son. The only drawback is the required ferry trip and associated schedule/steep prices.
12 - Old Croton Aqueduct
Winter (2016), okay hike done with 2 inches of snow on the ground. Spent most of our time at Croton Gorge Park at northern end of the trail. I’m unsure why this isn't included in any guidebook but within there is 200 ft. high damn with a large waterfall that interested my son. Also includes its own network of trails and a playground.
21 - Bear Mountain
Spring (2013), excellent hike with great views that the Catskills in the distance as well as all of the Hudson Highlands with the views of Anthony’s Nose and Popolopen Torne being highlights. On the summit are both some small scrambling opportunities and Perkin’s tower – my son liked both. At the trailhead is a playground, carousel, a zoo, and of course parking fees. Difficult but worth it with kids.
23 - Canada Hill
Fall (2014), okay hike with limited views of the Hudson. Hiked through the Russel Wright Design preserve found at a parking area which has a well established trail system with some mild highlights (lake, fire pits, etc.…). The trail from the preserve (Appalachian Trail) to Canada Hill lacks views and wasn’t interesting enough for my son.
24 - Bull Hill
Spring (2014), good hike with excellent views from summit area. Difficult but worth it with kids as the large abandoned query and a few ruins keep my son’s interest.
27 - The Palisades (2X)
Summer (2014), explored the Northern half with the usual suspects and my Brother who was in town. Good hike with good views of the Hudson from the ridgeline, a small castle to explore, and several nice spots to rest next to the Hudson River.
Summer (2015), explored Southern half of the hike detailed in the guidebook. Good hike right on Hudson with some views of Yonkers and a rough sand beach at the trailhead.
29 – Patterson/Garrett Mountain
Fall (2013), mediocre hike with some views of central jersey but lacks wilderness feel as it is swarmed by both people and vehicles. Better for kids with a few ponds and stone buildings which held his interest.

Otherbooks:

AMC'S Best day Hikes Near New York City, Daniel Case, AMC Books, 30/50 <60%>
16-Turkey Mountain
Fall (2015), good hike up to summit area with decent views of central Westchester County including the Croton reservoir. The hike was a good length for toddlers with apparently better views in fall/winter/spring.
19 – Ninham Mountain
Spring (2016), good hike up to the highest fire tower in NY State (90 ft.). The hike itself is rather mundane with a big pay off at the end. From the top you can see the NYC skyline, Hudson Highlands, gunks, Berkshires, and Catskills in what amounts to the best view in Putnam County that I’ve seen. My 4 year old made it to the top even though he was scared and hesitant throughout – once we’re back on terra firma he was quite proud he did it … the few other kids we saw all turned back.
32 – Ringwood Preserve
Spring (2016), good hike that toured skyline manor botanical garden (official NJ garden) and Halifax trail (white) up to Defiance Mountain. The botanical garden is top notch with multiple themed areas, fountains, and manor house. While not my cup of tea the family enjoyed it immensely (including the grandparents) while I also took a small side hike to Defiance Mountain.
38 - Massapequa Preserve
Fall (2015), average hike through forests and adjacent to Massapequa lake for the last mile. My son loved the birds/swans in the lake and we spent an extra half hour watching them.
40 - Manneto Hills
Winter (2016), mediocre hike with not much to reco77mmend (don't know how this makes the selection for a "best" day hike book review).
42 – Upland Farm Sanctuary to Cold Spring Harbor State Park
Spring (2016), mediocre hike with views of the sound that traversed several hills which mostly followed the Long Island Greenbelt trail. Took side trail to Upland Farm Sanctuary (which in my opinion lacks any points of interest – as all the cool areas are private property owned by Cold Spring Harbor) and returned. Lacks wilderness feel and the amount of people (in the triple digits) we saw was staggering. The highlight of the trip was a non-hiking side trip to the Cold Spring Harbor Aquarium.

Take a Hike New York City: 80 Hikes within 2 hours of Man…, Skip Card, Avalon Books, 33/80 <41%>
2,10 – Ringwood-Ramapo to Crossover
3,2 - Fire Tower Loop
Fall (2015), great hike up to a fire tower with good views of both Sterling and Greenwood lakes. At the time of our visit the fire tower was officially closed but we still made it up to the platform. The facilities around Sterling Lake are top notch with multiple old iron work buildings close by which my son enjoyed.

Best Hikes Near New York City, Ben Keene, American Hiking Society, 25/40 <63%>
9 - Cranberry Lake Preserve
Winter (2016), good hike that toured a large lake, bird watch, small waterfall, and an old mining query. Overall, the preserve is a small area that was good for an afternoon but probably not more. There was one inch of snow on the ground that my son enjoyed playing in. After the hike he said, "that was fun" – mission accomplished.
16 – Long Island Pine Barrens
Spring (2016), average hike which toured a “barren” pine forest. The pine forest itself is quite unique with withered pines, poor growing deciduous trees, and a limited understory. The hike lacks any destination or wilderness feel as it crosses over streets, powerlines, and railroad crossing but surprisingly my son loved it - running over the gentle hills and moss covered slopes.
30 – Monks Mountain
Spring (2016), average hike which circumnavigated Monks Mountain through a deciduous forest. The highlights are some good views of Monksville Reservoir and some detritus from a former iron mine.

Other areas (unguided)
1 – Sands Point (2X)


 

Quick Top 10 Lists/Peaks

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Northeast USA Drainage Basin High Points22.2
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Highest Peaks Climbed
PeakElev-ftLocationAscent Date
Pikes Peak14110USA-CO1996-08-01
San Jacinto Peak10839USA-CA2006-07-02
Haleakala10023USA-HI2004-07-01
Kettle Peak10004USA-CA2009-06-16
Tahquitz Peak8846USA-CA2003-06-01
Toro Peak8716USA-CA1997-06-01
Mount Williamson8214USA-CA2006-05-28
Suicide Rock7528USA-CA2006-01-14
Spitler Peak7440USA-CA1994-06-01
Thomas Mountain6825USA-CA2014-12-22
Most Prominent Peaks Climbed
PeakProm-ftLocationAscent Date
Haleakala10023USA-HI2004-07-01
San Jacinto Peak8319USA-CA2006-07-02
Mount Washington6148USA-NH2014-09-01
Pikes Peak5510USA-CO1996-08-01
Toro Peak3996USA-CA1997-06-01
Cuyamaca Peak2855USA-CA2006-02-26
Thomas Mountain1945USA-CA2014-12-22
San Gabriel Peak1561USA-CA2006-04-22
Volcan Mountain1559USA-CA2014-12-27
Cadillac Mountain1528USA-ME2014-08-26

     
    



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