Summary: Tons of fun and great views. This trail was a great way to spend a morning. Try to get there early, though, because I found that the parking area was full by about 10am. Watch out for hikers, horses, and dogs. I had someone's spooked dog run in front of me for almost 2 miles despite my best efforts to stop him. Don't expect anything very technical except for strecthes of sand along the coast. Even though the serpent's back trail was rated a black diamond, I would say that it would be an easy blue back in Colorado. Be sure to bring a camera.
Recommended Route: I rode two good loops. Even though I had an unexpected stop at the Montauk recycling center, I still enjoyed the first loop more. First loop: Begin at Hither Hills overlook. Ride the serpent's back trail north across the railroad tracks (at the fork immediately before the tracks go to the right). Once across the tracks you will hit the Old North Road which follows the coast. To go east continue straight. Going up the hill to your left will take you west. I road the Old North Road east all the way to the fishing pier, but be sure to stop along the way for photo ops. There is a confusing network of trails and roads behind Rod's Valley Park next to the fishing pier that landed me at the Montauk Recyling center. I took Old Montauk Road and Midland back to Flaggy Hole Road back to the power line road back to Hither Hills Overlook. Second loop: North on serpent's back to the Stephen Talkhouse trail (west on Old North Road) follow this all the way to Fresh Pond and then take Elisha's Valley and Petticoat Hill trails (parts of which are crumbling asphalt) back up to the overlook.
Other recommended trails in the same area: Northwest woods trails in Easthampton are also good. More woody, but not as many good views.
Review Date April 24, 2001
Overall Rating 5 of 5
Ridden Trail: Ridden Once
Visitors rate this review 5.00 of 5,
Reviewed by: CuirBoi
Summary: My first venture off road as a complete novice, too much fun! Cool gray spring Saturday, had trails to myself. Ride Guide and Falcon guide said it was intermediate riding, prepared to walk a lot but didn't have to. Lots of easily manageable doubletrack and singletrack, combined with bunches of more difficult singletrack. Balked at my first (short) steep rocky descent then got courage up and did all the others. Had one non-consensual horizontal dismount, imagine other beginners are likely to as well on some of what's here. If you're lucky you'll land on soft shoulder instead of less forgiving tree trunks and rocks and thorny bushes. Great adventure and schooling for this novice! Recommend long sleeves & eye protection for the thorns, patch kit for the thorns, helmet for tree trunks. Trail map at Overlook parking area complements Ride Guide map with trail names and more detail. Signs indicate *hunting* area in season, I'd get details before planning post-summer ride. 5 tires for atmospheric beginner adventure!
Recommended Route: Tried to follow first Hither Hills trip in Sendek's Ride Guide ... got lost, had fun. Enter Overlook Parking area on Rt. 27, follow Ride Guide directions until you make a left onto Floggy Hole Rd., search in vain for next intended left, find fun singletrack anyway, discover small logs are NYC curbs in camoflage, pop over at speed and feel like you know what you're doing, ride until you're worried about finding your way out in time for your train, go to highest spot you can find,locate doubletrack, cross fingers and follow, decide on later train and give in to more singletrack fun as you find it, somehow end up on Parkway Trail (parallel to Montauk Highway), follow east to recycling center and out. Too cool to swim and not go hypothermic on ride back to train? Console yourself with lunch/dinner at the Lobster Pot, best restaurant in Montauk!
Review Date March 18, 2001
Overall Rating 2 of 5
Ridden Trail: Every few months
Reviewed by: Bryan W
, from Southbridge,MA
Summary: This trail can be an extremely good workout for the advanced rider for keeping in shape if you wear a heart monitor and keep your cadence up,just do your race pace early in the morning,theres tons of novices out by the middle of the day!This trail is definatley non-technical and is more for beginner riders.And remember!1)pick up that trail map 2)look for ticks after the ride 3)watch for oncoming riders and hikers,it's very fast! I'm only giving 2 stars because of the lack of technical terrain,it gets 4.5 stars for speed though.
Recommended Route: 1)pickup a trail map at the Montauk chamber of commerce located right at rotary in downtown montauk.Why? becuase you should definately ride all the trails available and make up your own mind.If your in for speed,take the "flaggy hole rd" route in a westerly direction,you can average 20 mph plus easily for a little over a mile-very fast.There's also a neat little single track on the west side of the power lines that parallels the power lines.best done heading in a northerly direction.Now,cross the tracks and after about 3/4 of a mile,theres a fairly new single track that shoots off to the north off that road,take that in a westerly direction,when you get to a little sandy road,just take a quick left and then a quick right,and you can continue on that single track,you'll come to another sandy road,just take a quick right onto it and then followed by an immediate left,yup-back on that single track again.that will then take you back onto "old north rd." again,take left to the bottom of the hill and take another right,you'll be crossing the tracks again-go straight,if you have the trail map,you should be able to pick up the "flaggy hole rd." route.when you get to the end of that route,take a left,and you'll be back on the "old north rd." again.You'll want to eventually make your way over to the "lookout",start heading east,you can pick up the trail again right from that parking lot,take the "parkway" trail back to your vehicle,this trail paralells the "montauk hwy".
Review Date October 1, 2000
Overall Rating 4 of 5
Ridden Trail: Ridden Once
Reviewed by: Kevin & Marybeth Radics
, from Suffolk
Summary: We toured the unpaved roads. The puddles block some of the trails, but who does not like to get a little wet while biking. There are some good climbs and fast descents. Bring your GPS and wear bug spray. The trails are curved and some are overgrown. You can see deer, rabbits, and many birds. Good for all levels.
Recommended Route: Start at the beach and ride on Old Montauk Highway to the North trail acroos from the picnic area. Nice view of the Ocean from this trail because you are lower than 27. Cross over 27.
Other recommended trails in the same area: Stop in at Hither Hills Campground and pick up a free map. The trails are not marked so be careful and use your GPS to mark the path you choose. We did not.
Review Date September 16, 2000
Overall Rating 4 of 5
Ridden Trail: Every few months
Reviewed by: casey
, from nyc, ny, usa
Summary: i go to montauk a few weekends every summer. the riding in hither hills isn't as intense as, say, blue mt. in peekskill (westchester) but it's fun. the fort pond bay side has some nice small rolling hills thru the woods. there's a place where the trails hook up w/a 4x4 road that rolls out onto the beach (facing the sound)-- good spot to chill, eat a clif, take in the sound and gardiner's island, or maybe have non-riding friends meet you there for lunch. trail to goff point (called "coastal trail" i think) is closed because of fragile dune ecosystem. hither hills is fun cause you can take it easy & burn off the hangover or you can hit serpent's back if you want to huff a little more. watch out for ticks (check your crotch, they migrate to the warm spots), thorns (bring patches & maybe even a spare tube, i know from experience!!), and sandy spots. have a sunset chowder at duryea's or a more spendy family-style meal at the harvest. relax! 4 stars for fun, interesting landscape, proximity of cooling ocean water.
Recommended Route: probably best starting point is the overlook on rte 27 west of the town proper; i like the "keyhole" and "ironwood" sections but both are very short. most challenging trail is "serpent's back." maps for sale @ montauk bike shop or look in guide books.
Other recommended trails in the same area: i live in nyc and i like blue mt. reservation in peekskill; also see reviews of "da city."