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There are 12 valid routes plus one bonus route!
This 10.3 mile out-and-back route may be the shortest hike on this list, but it is by no means the easiest! The rugged trek described below features some of the toughest hiking, but also some of the greatest outdoor rewards in all of CT! With 3,400 ft of vertical elevation gain (and descent), this hike is sure to test your physical strength and endurance!
The hike begins at the Undermountain Path trailhead on Undermountain Rd in Salisbury CT. You will take the 2-mile Undermountain Trail uphill to the junction with the Appalachian Trail. Turn right (northbound) and proceed to the summit of Bear Mountain, the highest peak (but not the highest point) in CT at an elevation of 2,316 ft. Enjoy the stunning views from atop the remnants of the old stone tower, before continuing northbound down the steep north side of Bear Mountain. Please note that this section is extremely dangerous when wet or icy, so exercise extreme caution here.
Not long after the trail flattens out a bit, you will reach a trail junction with a sign pointing left (westbound) towards AMC’s Northwest Cabin (if you reach the Paradise Lane trail junction with signs for Sages Ravine, you have gone too far). Proceed left along the cabin trail to connect over to Mt Washington Rd at the MA/CT line. Make a slight right crossing the dirt road and you will find yourself at the Mt Frissell trailhead. The next 1.8 miles along the red-blazed trail to the tri-state marker of CT, MA, and NY are a fun roller coaster of scrambling, first up and over Round Mt, then to the summit of Mt. Frissell in MA, before descending slightly to the highest point in CT at an elevation of 2,380 ft on the south slope of Mt Frissell along the MA border. Very soon after, you will reach the tri-state marker and the turnaround point for this hike.
To successfully complete this route, you must return exactly the way in which you came. It is highly recommended however that you continue past the tri-state marker to the South Taconic Trail in NY, taking a left hand turn to head south to Brace Mt which has magnificent views of the Hudson River Valley. While a worthwhile and easy addition to this hike, it will add about two out-and-back miles to the trek outside of CT, and is therefore not required.
The Pachaug State Forest in far-eastern CT was once regarded as pure hellish by colonial settlers who found that the rocky landscape made farming, and therefore living, extremely difficult. Names such as ‟Hell Hollow” and ‟Mt. Misery” are derived from their early struggles to survive here. Today, this region of the state hosts many miles of excellent and relatively easy hiking trails through landscapes that are anything but hellish! However, the distance of this route will be the true challenge.
At 30 miles, this loop hike traverses large portions of the blue blazed Pachaug, Nehantic, and Quinebaug trails. While it is permitted to start anywhere along the loop, the recommended starting point is at the Tippecansett trailhead parking lot next to Beach Pond on Ten Rod Rd, just over the border in RI. If traveling counter-clockwise, leave the parking area and cross Ten Rod Rd, following the blue blazes of the Pachaug Trail (note that the yellow blazes correspond to the Tippecansett Trail).
Start by following the Pachaug trail for about 14 miles, passing a few notable points of interest such as the rugged shoreline of Beach Pond, Great Meadow Pond and the fear-inducing Hell Hollow until reaching a junction for the 0.8 mile red and blue blazed Quinebaug-Pachaug Crossover Trail. Turn right on this trail and follow it to the junction with the blue blazed Quinebaug Trail, turning left to then follow it approximately 1.8 miles to its terminus at the blue blazed Nehantic Trail. Turn left on the Nehantic Trail and proceed 2.8 miles to a junction with the Pachaug Trail. Don't let the eerie and abandoned farmhouse on Lee Rd frighten you - it is harmless!
At the Pachaug/Nehantic trail junction, turn left and continue along a path shared by both trails for 1.7 miles which includes a fun climb up Mt Misery and a rewarding vista at the top. Consider taking the 0.3 mile Rhododendron Sanctuary boardwalk spur at the Mt Misery Campground along this section, although this is not required to complete this route. When the Pachaug and Nehantic trails split just past the Mt Misery campground, turn right to stay on the Nehantic Trail for another 6.2 miles to its terminus at Green Falls Pond where it again meets the Pachaug Trail. The last stretch again follows the Pachaug Trail for 4.5 miles over some fun rocky terrain back to Beach Pond to finish the route.
No CT hiking challenge would be complete without including some of the iconic cliff-walks of CT's well known traprock range. The basalt rock that forms this range, known as traprock, was created long ago by volcanic activity, and is well known for the small cube-shaped pieces that it breaks off into which litter the Metacomet and Mattabesett trails. Subsequent tectonic activity has tilted the landscape along this range and formed dramatic westward facing cliffs spanning north to south across the center of the state and are prominently seen from many communities including New Haven, Hamden, Durham, Meriden, Southington, New Britain, and Simsbury. The rugged and dry terrain along these ridgelines, as well as the distance of this route, make this one of the more difficult hikes of this challenge. This is made up for however by many breath-taking views that are unbeatable by many other hikes in CT.
The 31 mile route from Mt Higby in Middlefield to Ragged Mt in Southington/Berlin is relatively straightforward, following the New England Trail for the majority of its length except at the very beginning and end of the route. The hike may be completed north or southbound and is only required to be completed in one direction (i.e. no out-and-back is necessary). If heading northbound, begin the hike at the paved parking area for Mt Higby on the westbound side of Route 66 in Middlefield. Take the 0.1 mile red and blue blazed spur trail to meet the blue blazed New England Trail, and turn left to proceed up to the ridgeline. From there, follow the blue blazes of the NET to Mt Higby, Chauncey Peak, Giuffrida Park, Lamentation Mt, the Hanging Hills/Castle Craig, Short Mt, and Ragged Mt, finally leaving the NET at the junction with the Orange and Blue blazed trail leading to the parking area on West Ln in Berlin. If heading southbound, begin at West Ln and follow the above directions in reverse.
Please note that a short section of the NET around the quarry to Chauncey Peak is currently closed. Until it is reopened, the acceptable detour follows the 0.1 mile red and blue blazed bypass trail. You should still do the very short out-and-back to hit the vista on Chauncey Peak however.
Along these trails, you’ll hike through diverse landscapes and incredibly challenging terrain, but will be rewarded with stellar views west towards the Catskills and Taconic mountain ranges. Don’t underestimate the difficulty of the western half of the park however, as the sections of the blue, green, and white trails that traverse this area are some of the steepest and most technically challenging trails in the state! The western half of the blue trail was also once part of the Appalachian Trail until it's reroute further east many years ago, but it is fun to imagine hiking along this stretch of rugged and technical trail on your way from Georgia to Maine at one time!
Macedonia Brook State Park in Kent is a CT hiking gem. Nestled in the rugged far western hills of the state, the park offers 12 miles of fun and challenging hiking trails, in addition to numerous camping opportunities. Spend a long weekend here and hike all 12 miles of these stunning trails! This challenge requires hiking each of the trails listed below in their entirety:
There is no required order nor direction in which to complete these trails - you have complete flexibility to choose your own route. Note that some backtracking will be required but part of the fun is deciding how to minimize it! One potential route is provided in the Strava link below.
The Housatonic Range Trail in New Milford, interestingly enough, does not often get much mention when discussing CT’s iconic hiking trails. In fact, aside from a few specific landmarks such as Tory’s Cave, Candlewood Mountain, and the infamous Corkscrew, much of this 6 mile trail appears to be little known and rarely hiked. On top of that, development has continued to encroach on the trail, truncating it over the years and rendering one section impassible since 2022 as newly built homes now stand where the trail once passed through. Despite these misfortunes, many fun and challenging sections of this trail remain and continue to rival some of the more well known trails in the state, making it a great Extreme CT hiking route!
This trail is more-or-less a simple out and back of a majority of the blue blazed HuRT. You may start and end at any point along the trail, but must complete the entire route in both directions, with a few small yet important exceptions described below. If starting the hike traveling southbound from Gaylord Rd, the route is defined as follows.
Start by proceeding 1.6 miles along the HuRT until reaching Squash Hollow Rd. Here, the HuRT turns left, but because of a housing development on Everwood Road that has interrupted the trail, the Extreme CT bypass of this section requires turning right instead and following Squash Hollow Rd for approximately 1.25 miles to rejoin the HuRT where it crosses the road again. Turn right at this point and proceed southbound again along the HuRT. Note that this also bypasses a section of the trail that travels near Tory’s Cave, the only marble solution cave in CT. While not necessarily worth going out of your way for as it is gated off to the public now, you may be interested in adding some additional out-and-back miles to check it out, but do not under any circumstances trespass on private property near Everwood Road.
After rejoining the trail, you’ll traverse a rugged yet seldom hiked section of the trail with a steep boulder scramble climb known as the Suicide Ledges. You must hike the Suicide Ledges in at least one direction, but may opt to hike the Blue/Green blazed bypass trail in the opposite direction if conditions are unfavorable as this is a very tricky section of trail. Eventually, the trail crosses Route 37 and makes its way towards the southern terminus on Candlewood Mountain, but not before forcing you up a tricky boulder scramble known as the Corkscrew. Similar to the Suicide Ledges, you must hike the corkscrew in at least one direction, but may opt to hike the bypass trail in the opposite direction if conditions are unfavorable.
Once you’ve reached the summit of Candlewood Mountain, you can begin the trip back northbound, with one exception. Just north of Candlewood mountain is a Blue/Red blazed loop called the Kelly Slide Trail, which brings you down and through a massive boulder slide on the eastern side of the mountain. You must hike this loop in one direction (northbound or southbound, not both), meaning that the short stretch of the HuRT between the two ends of the loop only needs to be hiked in one direction. From there, you must hike back the way you came (except if opting to bypass the Corkscrew or Suicide Ledges on the return trip) to Gaylord Rd.
As mentioned previously, you may also choose to start this hike somewhere in the middle (there is parking on Route 37), hike to either the northern or southern terminus, turn around and hike to the opposite terminus, and then turn around again to return to your vehicle at the midway point where you began.
The 20 mile Quinnipiac Trail has a claim to fame for being the first blue blazed trail developed and maintained by the Connecticut Forest and Park Association after its establishment in 1929. CFPA now maintains over 825 miles of blue blazed hiking trails across CT, and while this trail system has undergone some changes over the years, much of the original Quinnipiac Trail continues to be preserved today despite extensive urbanization in surrounding areas.
The Quinnipiac Trail is also indisputably one of the most challenging trails within the blue blazed hiking trail system. While not nearly the longest, it boasts challenging terrain along its entire length, as well as one of the scariest and steepest climbs in all of Sleeping Giant State Park. Hiking the five mile section of the trail within Sleeping Giant State Park is a daunting task all on its own - hiking the entire 20 mile trail in one go from Prospect to Hamden is downright extreme.
You may choose to hike this route in either direction, starting either at Hartford Turnpike in Hamden or Boardman Dr in Prospect, but it is highly recommended to leave a car at Boardman Dr and arrange for transportation to get you either to or from Hartford Turnpike, since there is no safe parking along Hartford Turnpike. If beginning your hike at Boardman Dr, you'll start the hike along a relatively new section of the trail opened just a few years ago bringing you through Kathan Woods, before joining the original trail 3 miles in to pass Roaring Brook Falls. This waterfall, the tallest single-drop waterfall in CT, is located a short distance off the trail along an orange blazed side trail. While not required for this route, it is a highly recommended detour. The trail then climbs Mt Sanford with a nice vista and proceeds south to High Rock near West Rock Ridge State Park where it meets the blue blazed Regicides Trail. Continue to follow the Quinnipiac Trail eastbound at this junction, since the Regicides trail continues further south along the ridgeline for 7 miles into New Haven.
The Quinnipiac then follows a series of ridgelines, interrupted occasionally by short roadwalks, before entering Sleeping Giant State Park and the most challenging part of the entire hike. The trail first takes on the Giant's Head with a very steep climb along the edge of a high traprock cliff where it is almost guaranteed that you will need to use all fours to safely reach the top. Beautiful views will reward you the entire way up however with a great vista on the Giant's Chin at the top of the climb. The trail hardly lets up however as it bounces along the Giant's Body to the stone tower. It is definitely recommended to climb to the top of the tower to enjoy great views of the park, the city of New Haven, and Long Island Sound. The remaining section of the trail to its terminus on Hartford Turnpike is not quite as difficult as the preceding section, but will certainly still test your endurance. This section of trail intersects many other trails in the park, so remain alert to sudden turns and to always follow the blue blazes.
The Tunxis Trail in Burlington is a maddening spider web of interconnected sections of blue blazed hiking trails crisscrossing the town. The route outlined below does not attempt to hit every section of this network, but instead will take you on a 19 mile loop highlighting some of the most scenic and challenging portions of this trail system.
You may begin this hike at any point along the loop, one such location being at a trailhead for the ‟Mile of Ledges” on East Plymouth Rd near Marsh Pond. Heading counterclockwise, enter the woods following the Blue/White trail which almost immediately terminates at an intersection with the mainline Tunxis Trail blazed solid blue. Continue straight and follow this trail for 0.7 miles to the junction with the Blue/Yellow trail's southern terminus. Turn right onto the Blue/Yellow trail and follow it for 3.5 miles through the Mile of Ledges and Session Woods to the first junction with the Blue/Orange Trail. This is the most challenging segment of the loop. The Mile of Ledges will force you to scramble and climb your way over steep and technical terrain, but if you can handle this, the rest of the hike will be a piece of cake!
At the junction with the Blue/Orange Trail, turn left and follow it for 3 miles through the Devil's Kitchen and into the Nassahegan State Forest where it terminates again at the Blue/Yellow trail. Turn right and proceed along the Blue/Yellow trail for 0.8 miles to the southern junction with the Blue/Purple Punch Brook Trail. Turn right and follow this trail for 1.5 miles until reaching the Blue/Yellow Trail again. Turn right and follow the Blue/Yellow trail one last time for 0.2 miles until reaching the junction with the Blue/White trail's northern terminus. Turn left to follow the Blue/White trail for 10 miles back to East Plymouth Rd. This trail can be difficult to follow at times, especially through the housing development on Johnnycake Mt where trail blazes can be difficult to find as the trail squeezes around houses and through a few backyards, but be diligent and you can find your way.
Bigelow Hollow State Park and the adjacent Nipmuck State Forest in Union host some of the finest hiking trails in northeastern CT. The 20 miles of interconnected blazed trails traverse a diverse landscape including mossy hemlock forests, wetlands, rocky ridgelines, and circle 3 large bodies of water - Bigelow Pond, Mashapaug Lake, and Breakneck Pond. This Extreme CT challenge requires hiking all 20 miles of blazed hiking trails listed below:
There is no required order nor direction in which to complete these trails - you have complete flexibility to choose your own route. Note that some backtracking will be required but part of the fun is deciding how to minimize it! One potential route is provided in the Strava link below.
The Leatherman was a celebrity vagabond in the northeast during the mid 1800s who walked a repeated 365 mile loop for many years without break between western CT and eastern NY. Dressed almost entirely in leather clothing, he would be easily recognized as he passed through the same towns roughly every five weeks for food and supplies. At night, he slept in caves and rock shelters along his circuit, one of which named the ‟Leatherman's Cave” in Thomaston CT will be a highlight of this Extreme CT route. Little was known about the Leatherman's personal life adding to the allure of this mysterious man who eventually died of mouth cancer after resisting medical treatment in favor of dying on his own terms along his circuitous hike.
While not at all the same route the Leatherman traveled, this 18 mile hike traverses challenging terrain and brings you through one of the famous caves frequented by the Leatherman for shelter. With the exception of a few rather lengthy roadwalks between trail sections, this route utilizes some phenomenal and seldom traveled sections of the Blue Blazed Mattatuck, Jericho, and Whitestone Cliff Trails in the towns of Plymouth and Thomaston.
You may begin your hike at any point along the route, but a recommended starting point is at the trailhead for the Whitestone Cliffs Trail on Route 262 in Plymouth. From here, it is suggested to travel counterclockwise, beginning with a 4 mile roadwalk up Greystone Rd to South Main St in order to connect to the Mattatuck trail. Upon reaching the Mattatuck Trail when it crosses South Main St, proceed westbound approximately 9 miles over a series of ridgelines and valleys to the Leatherman's Cave and Crane's Lookout. From here, leave the Mattatuck Trail and proceed southbound along the Jericho Trail for 3.1 miles to its southern terminus on Echo Lake Rd.
A short roadwalk is required here since the Jericho-Whitestone Cliffs Connector Trail is not being maintained and as of 2022 was incredibly unpleasant to navigate between the Jericho Trail and Route 8. Please do not take that section of trail. Instead, proceed eastbound up Echo Lake Rd and right before reaching Route 8, you'll see the Blue/Yellow Connector trail blazes appear and follow the road up to and over the Naugatuck River. Just after crossing the river, the trail drops down the embankment to the left and follows the river before making a hard right turn to go under Waterbury Rd through a culvert. If this proves too difficult to follow, you may also just walk north up Waterbury Rd to the sign for the Jericho-Whitestone Cliffs Connector Trail which resides above the culvert, and turn right to enter back into the woods.
The last stretch of this loop follows the J-WC Connector along an old trolley bed uphill to meet the Whitestone Cliffs Trail. At this junction, turn left to do the entire 1.3 mile Whitestone Cliffs loop, and once you've return back to the junction with the J-WC Connector, turn left to follow the blue blazes back to the WC trailhead to close the loop.
The longest route of the Extreme CT hiking challenge lies in the remote and seldom talked about “quiet corner” of CT out in the northeastern region of the state. While generally not considered a destination for extreme hiking due to its relatively easy and gentle terrain, the Extreme CT hiking challenge nonetheless ventures up to its neck of the woods to tackle a magnificent 45 mile loop in a remote and sadly overlooked region of the state.
This route showcases portions of three exquisite interconnected trails - the Nipmuck, Natchaug, and Airline Trails - forming a massive loop through some of CT’s finest woodland areas. You may start at any point along the loop as long as you complete it in its entirety in one trip, either as a multi-day backpacking adventure or an extreme single day sprint. The route description that follows assumes that you start at the Goodwin Conservation Center in Hampton CT and traverse the loop counterclockwise.
The southern terminus of the blue-blazed Natchaug Trail is located at a large parking area at the Goodwin Conservation Center headquarters on Potter Rd in Hampton. The first portion of the loop follows the entire 17.8 mile Natchaug Trail northbound through Hampton, Eastford, and Ashford to its northern terminus at the Nipmuck Trail. Along the way, you will enjoy stretches of deep wooded trail through pine and hardwood forests, pass numerous ponds and marshes, cross and follow countless rivers and streams, and encounter interesting landmarks such as the General Nathaniel Lyon Memorial Park and the Hole in the Wall Gang Camp.
At the northern end of the Natchaug Trail, make a left hand turn to follow the blue blazed Nipmuck Trail southbound for 16 miles to Mansfield where the trail splits into two southern forks. This stretch of trail is fantastic, as it begins by following a stretch of the 400 year old “Old Connecticut Path”, immediately followed by the beautiful Pixie Falls, and eventually making its way down to a 5 mile scenic stretch paralleling the Fenton River and passing very close by the University of Connecticut Storrs campus.
When the trail splits, continue straight to proceed 6.5 miles along the East Branch of the Nipmuck Trail towards Mansfield Hollow State Park. Almost immediately, the trail brings you to the top of “50 Foot Cliff” offering a beautiful sweeping view of the Fenton River valley towards Mansfield Hollow. Sit down on the bench here and take in the view before descending down a steep and rocky section and again following the Fenton River for another long stretch to Mansfield Hollow, where the trail then weaves its way amongst the many park trails and offers numerous views of the massive reservoir along the scenic shoreline.
The East Branch Nipmuck Trail’s southern terminus is at a large parking area on North Windham Rd in Mansfield. Turn left onto North Windham Rd, then right onto Mansfield Rd to cross over the Natchaug River (at which point the road turns into North Windham Rd Extension). Cross US Route 6 and proceed a very short distance up Route 203 to connect to the Airline State Park Trail and the final portion of the loop.
These last 4 miles are fortunately the easiest as you walk along the flat gravel bike path, a former historic railroad running between Boston and New Haven. Towards the end of this stretch of the loop, the trail crosses under Route 6 and then intersects Potter Rd. Turn right onto Potter Rd and return to the Goodwin Conservation Center Headquarters to finish the loop.
The penultimate route on this list of extreme CT hikes is a gift to any avid trail runners participating in the challenge. The Branford Trail is a quirky and little known 30 mile loop circling the town of Branford along the shoreline of CT, connecting woodland preserves and coastal parks. This trail is not a difficult one - in fact it is the easiest trail on this list! So what makes it Extreme CT worthy? The lack of available information about it, the significant sections of road walking (pavement is not friendly on tired feet after many miles of walking), and the probable need to complete this in a single day unless you can get creative with a legal overnight option on or near the trail. But these factors also combine to create the perfect trail if you enjoy trail running and will make this an easy route to check off this list!
As mentioned, little information is available about the loop as a whole. In fact, an entire section of the trail is completely missing from the map set available for download on the Branford Land Trust website. Fortunately, the trail itself is well marked with white circles along the majority of its length, but it is highly recommended to leverage the Strava map for this route, which can be recorded over for reference while completing this hike. Due to potential confusion however, additional leeway will be given for getting slightly off track so long as key sections of the route, outlined below, are hiked.
You may start at any point along the loop, but please note that some locations require a parking sticker available only to Branford residents (Branford point, for example), so one safe place to begin is at the Stoney Creek Quarry Preserve parking area on Leetes Island Rd (please note that while the Strava map has the start and finish at Branford Point, this is not a feasible option for most people). The description that follows assumes a counterclockwise hike from this location.
On the Branford Land Trust website, the first map to refer to is the Stony Creek section. Note that this trail description begins approximately halfway along this section, heading northbound from Leetes Island Rd towards Stony Creek Preserve. The downloadable pdf gives an adequate description of this section of the trail through a pleasant, although potentially muddy woodland area. This trail section leads naturally to the Quarry Westwoods section, a scenic and fun portion of the trail that traverses a ravine and gorge before briefly entering into Guilford and beginning one of many roadwalk sections, which bring the trail back into the Branford briefly and then into North Branford to begin the Northern Boundary section. The downloadable pdf for this section gives a good description of what to expect along this stretch of trail as it winds through a mixed bag of woodlands, wetlands, roads, business parking lots, and even a retirement care facility. The next section of the trail is the Pisgah Brook section which passes through Pisgah Brook and Saltonstall Mountain Preserve. Again, the downloadable pdf for this section gives a good description of what to expect along this stretch of the trail.
The section that follows - Lake Saltonstall - as the trail begins to turn southbound on the western side of Branford, has the very important consideration that a permit is required to hike on Regional Water Authority land. You are required to hike through this section to successfully complete this route per Extreme CT rules (you may not bypass this section of trail on Hosley Rd), so please plan ahead by calling RWA to obtain a permit at (203)-401-2654.
Continue on to the Short Beach section of the trail, where the trail first passes through Beacon Hill Preserve, then along a trolley line to Short Beach, and finally follows roads to Parker Memorial Park and a break in the trail at Branford Point. The official trail picks up again on the other side of the Harbor at Riverside Terrace on Indian Neck, however two issues arise for the purpose of making this a doable loop - one that there is no way to cross the harbor, and two that the section of trail that picks up on the other side does not have a map available on the Branford Land Trust website. Therefore, significant leeway will be given to connect to the Pine Orchard section of the trail beginning at Pine Orchard Rd. A suggested route is as follows. From Branford Point, proceed north up Harbor St to Maple St and turn right. Then make a right onto Indian Neck Ave and follow to South Montowese Rd, turning left and then making a right onto Ark Rd. At the end of Ark Rd, cross Tabor St and follow the Shoreline Greenway Trail to Pine Orchard Rd where you will rejoin the Branford Trail at the start of the Pine Orchard section.
Continuing along the shoreline, this next section of the loop follows a historic trolley line through tidal marsh areas and is an iconic Branford hike! Finally, the home stretch of this loop comes full circle back to the Stony Creek section of the trail, following roads and passing through a few preserves before finally reaching Leetes Island Rd to close the loop.
The most difficult among the main list of twelve routes for the Extreme CT Challenge, this route is rivaled only by the bonus Sleeping Giant Marathoner route. Combining extreme distance and elevation, completion of this hike will require hiking 34 miles with over 7,000 feet of vertical elevation gain (and descent) along the entire 24 mile blue blazed Mohawk Trail and a challenging 10 mile section of the Appalachian Trail.
You may start this hike at any point along the route, but the description below will assume that you begin at the Mohawk trailhead on Route 7 in Cornwall Bridge, heading counterclockwise. Immediately after crossing the bridge over the Housatonic River, the trail has been rerouted due to a closure from Dark Entry Rd to Coltsfoot Mt, so the official Mohawk Trail now turns left onto Brook Rd right where Routes 4 and 7 split and shortly after turns right to follow Popple Swamp Rd for 3 miles to where it rejoins Route 4. Turn right onto Route 4 for about 0.15 miles and make a left turn to enter back into the woods and rejoin the original Mohawk Trail in 0.65 miles. The new route should be blazed blue.
From here, follow the Mohawk Trail for about 19 miles until it reaches its northern terminus at the Appalachian Trail in Falls Village. Along this rugged stretch, you will first traverse a lovely section of trail through the Mohawk State Forest with notable points of interest being the popular Mohawk ski area and an excellent vista looking out towards Bear Mountain and the rest of the Taconic Range. The blue blazed Mattatuck Trail intersects with the Mohawk Trail here, and while not required, taking it 1.5 miles southbound will bring you past the Cunningham tower and eventually up to the top of Mohawk Mountain with sweeping 360 degree views, if you are up for a fun side trip.
After crossing Route 4, the trail travels north towards the Housatonic State Forest, passing over Red Mountain and Overlook Mountain. Once reaching the Housatonic State Forest, the trail swings westbound passing Music Mountain and eventually reaching Dean’s Ravine, praised as one of the best waterfall hikes in CT. Finally, the Mohawk trail climbs steeply to the top of Barrack Mountain with excellent southward facing views, before dropping steeply on the other side of the mountain, crossing Route 7, and intersecting the Appalachian Trail at the Warren Turnpike.
At this point, turn left and follow the AT southbound for about 10 miles until it intersects with the southern terminus of the Mohawk Trail near Breadloaf Mountain. This rugged section of the trail is mostly wooded with occasional vistas such as the Hang Glider View which overlooks the Limerock Racetrack, as well as a great eastward facing view from the top of Sharon Mountain, shared with the Pine Knob Loop Trail. On a clear day, one can also see all the way to the Catskills through the trees near Mount Easter. This section of trail also passes through the “Lemon Squeezer”, which is a narrow and steep passage between two massive boulders on the way down to West Cornwall Road.
At the junction with the Mohawk Trail, turn left and in 0.1 miles, enjoy a southward facing view from Breadloaf Mountain. Finally, proceed 0.7 miles down towards Route 7 to complete the loop.
Think you have what it takes to hike all 32 miles of the marked hiking trails in Sleeping Giant State Park in a single day? This logistical nightmare of a challenge has only been completed by a handful of elite Giant Masters. While the park boasts 32 unique miles of marked trails, successfully hiking all of them in one day will require backtracking and roadwalking which could bring total mileage up to as much as 40 with at least 8,000 feet of vertical elevation gain.
There is no single best way to complete this route. One possible strategy is provided in the Strava link below, but it is by no means proven to be the best or most efficient approach so it is encouraged to consider other strategies to completing this challenge. Regardless of how one decides to approach this, the following trails must be hiked in their entirety during daylight hours or the attempt will not be valid:
Successfully completing this challenge will not only earn you the status of a Giant Master Marathoner recognized by the Sleeping Giant Park Association (if already a member of SGPA), but will be worth TWO hikes towards the Extreme CT Challenge. In other words, completing this challenge will mean only needing to choose eight of the other twelve Extreme CT routes.
For more information of SGPA’s Giant Master program, please visit their website.