Sky's the Limit

Sky’s the Limit Hiking Challenge

The Sky’s the Limit Hiking Challenge is a program put on annually by the DEEP since 2015.  Each year DEEP staff pick 14 locations around the state to explore some element of the park.  To participate, hikers must take photos of at least 2 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 14 puts you in a drawing to win one of 50 hand-carved hiking staffs announced 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.

Former Challenge Lists

2015 Theme - Towers and Lookouts

(DEEP Archive Link)

  • 1: Talcott Mountain State Park, Simsbury/Bloomfield
  • 2: Haystack Mountain State Park, Norfolk
  • 3: Dennis Hill State Park, Norfolk
  • 4: Southford Falls State Park, Southbury
  • 5: Hurd State Park, East Hampton
  • 6: Shenipsit State Forest (Soapstone Mtn.), Somers
  • 7: Sleeping Giant State Park, Hamden
  • 8: Lovers Leap State Park,
  • 9: Macedonia Brook State Park,
  • 10: West Rock Ridge State Park,
  • 11: Mohawk Mountain State Forest,
  • 12: Mount Tom State Park,
  • 13: Fort Griswold Battlefield State Park, Groton
  • 14: Pachuag State Forest (Mount Misery), Voluntown

2016 Theme - Bodies of Water

(DEEP Archive Link)

  • 1. Dinosaur State Park, Rocky Hill
  • 2. Collis P. Huntington State Park, Redding
  • 3. Burr Pond State Park, Torrington
  • 4. American Legion State Forest, Barkhamsted
  • 5. Mansfield Hollow State Park, Windham/Mansfield
  • 6. Black Rock State Park, Watertown
  • 7. James L. Goodwin Forest, Hampton
  • 8. Windsor Locks Canal Trail State Park, Windsor Locks/Suffield
  • 9. Squantz Pond State Park, New Fairfield
  • 10. Millers Pond State Park, Duham/Haddam
  • 11. Mianus River State Park, Stamford
  • 12. Air Line State Park Trail (CTMARI Tri-point), Thompson
  • 13. Devil’s Hopyard State Park, East Haddam
  • 14. Bluff Point State Park, Groton

2017 Theme - Historic Sites

(DEEP Archive Link)

  • 1. Stratton Brook State Park (Stratton Brook Depot), Simsbury
  • 2. Bolton Notch State Park (Hop River Trail), Bolton
  • 3. Beckley Furnace Industrial Monument, East Canaan
  • 4. Topsmead State Forest (Barbeque Pit), Litchfield
  • 5. Bigelow Hollow State Park (Mashapaug Pond), Union
  • 6. Natchaug State Forest (Nathaniel Lyon Birthplace), Eastford
  • 7. Indian Well State Park (The Well), Shelton
  • 8. Air Line State Park, Blackledge River Bridge, Colchester
  • 9. Haley Farm State Park (Canopy Rock), Groton
  • 10. Gillette Castle State Park (Gillette Railroad Tunnel), East Haddam
  • 11. Chatfield Hollow State Park (Oak Lodge Nature Center), Killingworth
  • 12. Mashamoquet Brook State Park (Wolf Den), Pomfret
  • 13. Farmington Canal State Park Trail (Lock 12), Cheshire
  • 14. Putnam Memorial State Park (Officer’s Quarters/Magazine), Redding/Bethel

2018 Theme - “Lesser-known” Parks and Trails

(DEEP Archive Link)

  • 1. Housatonic Meadows State Park, Sharon
  • 2. Cockaponset State Forest, Guilford
  • 3. Naugatuck State Forest, Ansonia
  • 4. Seth Low Pierrepont State Park Reserve, Ridgefield
  • 5. Old Furnance State Park, Killingly
  • 6. Moosup Valley State Park Trail, Plainfield/Sterling
  • 7. Paugussett State Forest, Newtown
  • 8. River Highlands State Park, Cromwell
  • 9. Farm River State Park, East Haven
  • 10. Machimoodus State Park, Moodus
  • 11. Hopeville Pond State Park, Griswold
  • 12. Sunnybrook State Park, Torrington
  • 13. Day Pond State Park, Colchester
  • 14. George Dudley Seymour State Park, Haddam

2019 Theme - Staff Picks

(DEEP Archive Link)

  • 1. Mohawk State Forest, Sharon
  • 2. Kettletown State Park, Southbury
  • 3. Rocky Neck State Park, East Lyme
  • 4. Barn Island Wildlife Management Area, Stonington
  • 5. James L. Goodwin State Forest, Hampton
  • 6. Pachaug State Forest – Green Falls Area, Voluntown
  • 7. Salt Rock Campground, Sprague
  • 8. Mount Tom State Park, Litchfield
  • 9. Harkness Memorial State Park, Waterford
  • 10. Wadsworth Falls State Park, Middletown
  • 11. American Legion and Peoples State Forest, Barkhamsted
  • 12. Macedonia Brook State Park, Kent
  • 13. Dennis Hill State Park, Norfolk
  • 14. Horse Guard State Park, Avon

2020 Theme - DIY 'Paths Less Traveled'

(DEEP 2020 Link)

This year’s theme was supposed to be ‘Bridges and Boardwalks’ but was delayed until October 5th and was changed to 9 locations of your choice:

  • 3 State Parks
  • 3 State Forests
  • 3 Blue Blue Blazed Hiking Trails


2021 Theme – Bridges, Footbridges, and Boardwalks

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.

2021 DEEP Guide to Parks and Photo Locations

  1. Dinosaur State Park
    • 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
  2. Lovers Leap State Park
    • Photo Locations (4): Iron Bridge, Highlights of Lovers Leap State Park Interpretive sign, Indian Spring House, photo of your choosing
  3. Silver Sands State Park
    • Photo Locations (2):  New Concession building, Bench with viewing scope on the boardwalk
  4. Hammonasset State Park
    • 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
  5. Black Rock State Park
    • Photo Locations (3):  Footbridge, Bridge, photo from the area labeled on the map as scenic vista
  6. Chatfield Hollow State Park
    • 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
  7. Collis P. Huntington State Park
    • 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)
  8. Southford Falls State Park
    • Photo Locations (3):  Covered Red Bridge, bridge near parking lot, boardwalk on the Red Trail
  9. Wharton Brook State Park
    • Photo Locations (2):  Bridge over Wharton Brook and the Pitch Pine Natural Area Preserve sign
  10. Wadsworth Falls State Park
    • Photo Locations (2):  Covered Bridge and the stone arch bridge
  11. 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
  12. Ferry Landing State Park
    • 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
  13. Kent Falls State Park
    • Photo Locations (3):  Covered Red Bridge, timber footbridge, Bridge on Dugan Road (at the end of the Red Trail)
  14. Cockaponset State Forest
    • Photo Locations (4): 2 bridge locations/crossings along the Blue Trail, Collier’s Hut Remains, and Observation Tower Remnants
  15. Sherwood Island State Park
    • Photo Locations (3): Living 9/11 memorial, 2 locations (stops) along the Nature Trail
  16. Devil’s Hopyard State Park
    • Photo Locations (2): Covered bridge along the Eight Mile River, and a photo taken from the area marked on the map as Scenic View
  17. Stratton Brook State Park
    • Photo Locations (2): Covered Bridge and the timber boardwalk on the Orange Trail
  18. Salmon River State Forest
    • Photo Locations (2): Covered bridgearea labeled Salmon River Trail Scenic Vista
  19. Osbornedale State Park
    • Photo Locations (3): Boardwalk/footbridge across from Osborne Homestead Museum, a geologic feature found along the Red Trail, and boardwalk located along the trail
  20. Rocky Neck State Park
    • Photo Locations (4): Anywhere on the beach boardwalkBride Brook, intersection of the White/Purple Trail, intersection White/Red Trail

Southford Falls


41.458784, -73.163979

Southford Falls State Park Connecticut State Park 169 acres in Southbury and Oxford, CT Parking: Large lot near 175 Quaker Farms Rd, Southbury, CT Trail Map   … Read more…

Dinosaur State Park


400 West St, Rocky Hill, CT 06067

Dinosaur State Park Connecticut State Park 80 acres in Rocky Hill, CT Parking: Large lot at 400 West St, Rocky Hill, CT Trail Map         … Read more…