The Sky’s the Limit Hiking Challenge is a program put on annually by the DEEP since 2015. Each year DEEP staff pick 15 locations (upped from 14 to 20 in 2021-22) around the state to explore some element of the park around a common theme. To participate, hikers must take photos of designated locations within each park and submit them before the deadline.
Hiking and photographing 10 of the chosen parks will earn a medallion or lapel pin and certificate. Completing all 15 puts you in a drawing to win one of 50 hand-carved hiking staffs announced at a First Day event on January 1st of the following year.
I have participated each year, but visited only a handful every time. 2019 was my first year completing the challenge and I made a movie documenting it.
2024 Sky’s the Limit Challenge
Theme – “CT State Forests”
Pootatuck State Forest – New Fairfield, CT
Trails:
Option 1 is 6 miles on the CCC/Forest Road – take white/grey trail (forest/CCC road) starting off of Pine Hill Road following it to Short Wood Road (green gate CCC road entrance) and then turn around and head back.
Option 2 is 2.8 miles on the CCC/Forest Road/Orange/Yellow and Blue Trails – take white/grey trail (forest/CCC road) starting off of Pine Hill Road following it to Short Wood Road (green gate CCC road entrance) and then turn around and head back.
Photos: Participants choose one trail and take a photo of the signage/kiosk; photograph looking out at the Rock Lookout; and a photo of the participants choosing from along the trail.
Trail: Hike the blue blaze Nipmuck Trail to the Blue/White Dot Breakneck Pond View Trail about for at least 3 miles round trip
Photos: Take a photo of the signage/kiosk; a photo of Breakneck Pond; a photo of the waterbody, and a photo of the participants choosing from along the trail.
Trail: Take the blue blazed Shenipsit Trail (starting from the parking area off of Gulf Road) to the Blue/Green Trail up and over the Soapstone Mountain observation tower for a minimum of 1.7 miles lasso loop
Photos: Take photos of signage/kiosk; photo from the observation tower; photo from along the trail.
Trails:Green Fall Pond Loop (Blue and Blue Orange Green Fall Loop Trail) AND the Firetower Road/Mt. Misery and Cutoff Road loop for a total of nearly 5 miles
Photo of a sign/signage/kiosk; take a photo from somewhere along the Green Fall Pond Trail as well as from the area of Mt. Misery; and a photo of the participants choosing from along one of the 2 trails on-site.
Massacoe State Forest – Simsbury, CT
Trail: Great Pond Loop Trail (grey trail on map) about a 1.5 mile loop
Photos: Photo of sign/signage/kiosk; photo of a tree along the trail that catches the participants’ eye; and a photo of the participants choosing from along the trail.
Paugussett State Forest – Newtown, CT
Trail: Lillinonah Trail for as much you want up to 12 miles out and back
Photos: Photo of the sign/signage/kiosk, photo of Lake Lillinonah and a photo of the participants choosing from along trail.
Trail: Blue Trail (Jericho Trail) up to the Leatherman Cave for 6.6 miles out and back
Photos: Sign/signage/kiosk, photo from the Leatherman Cave; and a photo of the participants choosing from along the trail.
Nassahegon State Forest – Burlington, CT
Trail: Punch Brook Trail (Blue/Purple and Blue Yellow Trails) off of Punch Brook Road for approximately 3 miles out and back
Photos: Photo of the sign/signage/kiosk, feature along the trail (tree, rock, water area); photo of the participants choosing from along the trail or the lake.
Naugatuck State Forest – Bethany, CT
Trail: Tobys Rock Mountain Outer Loop for 2.7 miles
Photos: Photo of the sign/signage/kiosk, photo of a bird you see in the forest using the Naugatuck State Forest Bird Checklist; and a photo of the participants choosing along the trail
Trail: Blue blazed Salmon River Trail North Loop to the Day Pond Brook Spur Trail for about a 2.5 mile loop
Photos: Photo of the sign/signage or kiosk; photo of the waterfall; and a photo of the participants choosing from along the trail.
Topsmead State Forest – Litchfield, CT
Trail: Follow Chase Road to Jefferson Road, take the Bernard Stairs Trail; follow Jefferson Hill Road, take the Yellow Trail; follow Jefferson Hill Road South to the Chase Connector to Chase Road back to the parking lot for about 3 miles
Photos: Photo of the sign/signage or kiosk; photo from the Bernard Stairs Trail; and a photo from the Yellow Trail.
This year the total number of hikes has increased to 20. Completing all 20 will make you eligible to win one of 50 hiking staffs and completing 15 will receive a medallion and certificate.
Photo Locations (5): Trail information building, boardwalk at start, pick one of the Interpretive signs on the trail, decorated bat box, boardwalk on blue trail
Photo Locations (3): Plaque on the rock before heading onto the trail, photo looking out from the viewing platform towards Long Island Sound, interpretive signage on the viewing platform
Photo Locations (4): The History of Chatfield Hollow and The Paul F. Wildermann Boardwalk interpretive sign, Red Covered Bridge, any other bridge, footbridge or boardwalk along the hiking/walking area
Photo Locations (2): Trail bridge of your choosing and the Collis P. Huntington State Park signage with hand drawn trails and hand drawn explanation (key)
Photo Locations (2): Covered Bridge and the stone arch bridge
Peoples State Forest
Photo Locations (3): Agnes Bowen Trail/Robert Ross Trail signs, pick one of the Interpretive signs leading to or on the boardwalk/viewing platform, view out into the wetland along the boardwalk
Photo Locations (5): Photo of How Well Do you Know Boating kiosk, photo of railroad bridge, photo of Blue Crab Regulations sign, photo of osprey platform Interpretive signage with island/osprey platform in background; and photo of the CT River from anywhere along the timber walkway or timber boardwalk
Photo Locations (3): Boardwalk/footbridge across from Osborne Homestead Museum, a geologic feature found along the Red Trail, and boardwalk located along the trail
2022’s theme was ‘Best Kept Secrets‘. Hike and photograph 15 for a certificate and medallion. Hike and photograph all 20 to enter a drawing to win one of 50 hand carved hiking staffs. All entries were due by 3 pm on Friday, December 2, 2022.
Trail Names: Purple Trail – Train Tunnel Trail (1.14 miles) and the Blue Trail (.34 miles) leading down to the CT River.
Photo Locations (4): Gillette Castle signage, Gillette Castle, the train tunnel on Purple Trail, Osaki House and Aunt Polly by the water (best to see at low tide)
Trail Names: Richard D. Haley Nature Plant Wildlife Gardens and the .5 mile Forest Discovery Trail
Photo Locations (3): Goodwin State Forest or James L. Goodwin Conservation signage, anywhere within the Richard D. Haley Nature Plant Wildlife Garden, any area of the Forest Discovery Trail
Trail Names: Red Trail (1 mile) and the Edith Morton Chase Ecology Trail (.7 miles)
Photo Locations (3): Topsmead State Forest signage, signage inside of the viewing stand, one of the interpretive signs on the Edith Morton Chase Ecology Trail
Trail Name: Gravel Road (3.45 miles) in Bluff Point
Photo Locations (4): Bluff Point State Park signage, photo of the scenic view at the end of Bluff Point (shown as scenic view on the map), Sunset Rock (as shown on map) and Winthrop House foundation and signage
Trail Name: Take the Harkness Memorial Loop (1.3 mile) and the Niering Walk (.25 miles)
Photo Locations (5): Harkness Memorial State Park signage, photo from the Wildlife Viewing Platform on the Niering Walk, photo of/from the boardwalk as shown on the map, photo of one of the gardens, and a photo of the Mansion known as Eolia
Trail Name: Yellow Trail to the Flood Control Levee (1.75 miles)
Photo Locations (3): Mansfield Hollow State Park signage, Flood Control Levee signage, photo from any location looking out along/from the Flood Control Levee
Trail Name: Hop River State Park Trail starting in Bolton Notch State Park (4.5 miles)
Photo Locations (5): Bolton Notch State park signage, Hop River State Park signage, Bolton Notch tunnel, photo of a rock formation along the trail, photo of an interesting “find” along the trail (could be anything-the trail, an animal, building, tree, etc.)
Trail Name: Red Trail to White Trail looping around Lake Wintergreen
Photo Locations (3): Lake Wintergreen signage, view of Lake Wintergreen from the trail, photo of an interesting feature or find on your hike (i.e teepees, animals, trees or tree root, etc.)
Trail Name: Six stop cell phone walking tour of Fort Griswold (.5 miles)
Photo Locations (4): Fort Griswold Battlefield State Park signage, photo of the monument or looking out from the monument, cell phone tour post and signage, view looking out from the constructed deck at Fort Griswold of the property
Trail Names: Shoreline Greenway Trail ( .6 miles) and the Farm River Nature Trail Please note: best to do during low tide conditions.
Photo Locations (4): Farm River State Park signage, Shoreline Greenway Trail signage, photo taken along the Shoreline Greenway Trail, and a photo taken along the Nature Trail
Trail Name: Gravel Road loop and loop around the Museum (1 mile)
Photo Locations (5): Putnam Memorial State Park signage, photos of 3 of the marked historic sites on-site (3 photos), and any other photo of your choosing
Trail Name: Walk the monument grounds at Beckley Furnace and visit the Industrial Monument (.25 miles)
Photo Locations (3): Beckley Furnace Industrial Monument signage, Beckley Iron Furnace, any other photo of the grounds or the furnace
For the 20th hike choose your own favorite CT State Park or Forest location, a feature within such park or forest, or what trail you feel is the “Best Kept Secret” here in CT. Please tell us the location, why it’s the Best Kept Secret” and share your photos with us. We are looking forward to hearing from you!**
2023 Theme - 'In, Under, Over or Through'
2023’s theme was ‘In, Under, Over or Through’ featuring five rails-to-trails and ten state parks. Hike and photograph 10 for a certificate and medallion. Hike and photograph all 15 to enter a drawing to win one of 50 hand carved hiking staffs. All entries were due by 3 pm on Friday, December 1st, 2023 ideally through the official Google Form.
Air Line State Park Trail in Portland, East Hampton, Colchester, Hebron, Columbia, Lebanon, Windham, Chaplin, Hampton, Pomfret, Putnam, and Thompson
Trail Name: Air Line Trail State Park
3 Photo Locations: Air Line State Park Trail sign/signage/kiosk, feature along the trail (i.e bridge, tunnel, stonework, stand of trees, wall, pond, stream, gate, path, building, etc.), photo of the participants choosing from along the trail
Larkin State Park Trail in Middlebury, Naugatuck, Oxford, and Southbury
Trail Name: Larkin State Park Trail
3 Photo Locations: Larkin State Park Trail sign/signage/kiosk, feature along the trail (i.e bridge, tunnel, stonework, stand of trees, wall, pond, stream, gate, path, building, etc.), photo of the participants choosing from along the trail
3 Photo Locations: Moosup State Park Trail sign/signage/kiosk, feature along the trail (i.e bridge, tunnel, stonework, stand of trees, wall, pond, stream, gate, path, building, etc.), photo of the participants choosing from along the trail
Farmington Canal Heritage Trail in Avon, Burlington, Canton, Cheshire
Trail Name: Farmington Canal Heritage Trail
3 Photo Locations: Farmington Canal Heritage Trail sign/signage/kiosk, feature along the trail (i.e bridge, tunnel, stonework, stand of trees, wall, pond, stream, gate, path, building, etc.), photo of the participants choosing from along the trail.
3 Photo Locations: Hop River State Park Trail sign/signage/kiosk, feature along the trail (i.e bridge, tunnel, stonework, stand of trees, wall, pond, stream, gate, path, building, open space area, etc.), photo of the participants choosing from along the trail.
3 Photo Locations: Auerfarm State Park sign/signage/kiosk, take a photo from somewhere along the Farm Trail (ideas for potential photos-apple barn, birds, wildflowers, etc.), and a photo of the participants choosing from along one of the 5 trails on-site.
Trail Name(s): Windsor Locks Canal State Park Trail
3 Photo Locations: Windsor Locks Canal State Park Trail sign/signage/kiosk, feature along the trail (i.e bridge, stonework, stand of trees, wall, CT River, fence, gate, building), photo of the participants choosing from along the trail.
3 Photo Locations: Mianus River State Park sign/signage/kiosk, Point of Interest along the Nature Trail, and a photo of the participants choosing from along the Nature Trail or within the park.
3 Photo Locations: Mount Riga State Park or Undermountain Trail sign/signage/kiosk, interesting feature along the trail or a view from the top of the trail, and a photo of the participants choosing from along the trail
3 Photo Locations: Hopemead State Park sign/signage/kiosk, stone chamber/root cellar, photo of the participants choosing from along the trail or the lake.
3 Photo Locations: Camp Columbia State Park sign, signage, kiosk, Observation Tower inside/outside or photo of the view from the Observation Tower, photo of the participants choosing from along the Red Trail
3 Photo Locations: Mount Tom State Park sign/signage/kiosk, Stone Tower inside/outside or photo taken looking out from the Tower, photo of the participants choosing from anywhere along the trail
3 Photo Locations: Haystack Mountain State Park sign/signage/kiosk, Stone Tower at the summit or photo taken looking out from the Tower, photo of the participants choosing from anywhere along the trail
3 Photo Locations: Chatfield Hollow State Park sign/signage or kiosk, pick your favorite cave and take a photo of it, photo of the participants choosing from anywhere along the Green Trail/Cave trail or along another trail in the park
Trail Names: Upper Vista Trail, Purple Trail and Lower Vista Trail
3 Photo Locations: Machimoodus State Park sign/signage or kiosk, photo of the participants choosing anywhere along the Upper Vista Trail, photo of the participants choosing anywhere along the Lower Vista Trail (scenic viewing areas are recommended)
Green Fall Pond Connecticut State Forest and Blue Blaze Trail 200 acres in Voluntown, CT Parking: Large lot near Green Fall Pond Rd, Voluntown, CT Trail Map …Read more…
Natchaug State Forest Connecticut State Forest 13,438 acres in Chaplin, Eastford, and Hampton CT Parking: Plenty of parking down the road near 243 Chaplin Rd Eastford, CT Trail Map …Read more…
Soapstone Mountain Connecticut State Forest 1800 acres in Ellington, Somers, and Stafford, CT Parking: Medium sized lot near 399 Gulf Rd, Somers, CT Trail Map …
Bigelow Hollow State Park Connecticut State Park / Nipmuck State Forest 516 acres in Union, CT Parking: Several large lots along the park’s road off CT-171. Trail…Read more…
Day Pond State Park / Salmon River State Forest / Comstock Covered Bridge Connecticut State Park and State Forest 180 acres in Colchester, CT Parking: Day Pond…
