CONNECTICUT'S LOOKOUTS & TOWERS
ORENAUG PARK FIRE TOWER
Woodbury, Connecticut
ABOUT THE HIKE
Built in 1911, the Orenaug Fire Tower offers amazing panoramic views of the Pomperaug River Valley. The ascent from the tower’s base is not for the faint of heart. It’s a steep, 80 foot climb to the top!
Take the orange, yellow or red trail for an out-and-back hike to the tower. I enjoyed the red trail because it offers multiple view points along the way.
DISTANCE: 0.9 miles on the orange trail & 1.1 miles on the red trail.
LEVEL OF DIFFICULTY: Easy / Moderate
PARKING
There are four parking lots with access to the trails at Orenaug Park: two near the Woodbury Senior Community Center located at 281 Main Street South, one at the corner of Orenaug Avenue and Park Road, and another at approximately 45 Park Lane.
Hikers can reach the fire tower from any of the parking lots. The shortest hike is from either of the lots on Main Street South and the longest is from the corner of Orenaug Avenue and Park Road.
CAMP COLUMBIA TOWER
Morris, Connecticut
ABOUT THE HIKE
If Camp Columbia State Park & Forest isn’t on your Connecticut bucket list, it should be! A short and easy trail brings visitors to a beautiful stone observation tower. A staircase leads to the top of the structure for a stunning 360 degree view.
In 1885, the Columbia College Engineering School of Plane Surveying began teaching summer classes on a plot of land close to Bantam Lake. The number of students increased to nearly 200 by 1903.
During the First World War the Camp became a military combat training facility for Columbia students planning to join the conflict. Over 300 yards of trenches were dug into the property to help prepare the future soldiers.
The property returned to its original mission as a summer camp after the war. The gorgeous stone tower that visitors to Camp Columbia State Park enjoy today was built in 1942 as a gift from the Class of 1906.
DISTANCE: 0.5 miles
LEVEL OF DIFFICULTY: Easy
PARKING
Camp Columbia State Park has one main parking lot at 294 West Street in Morris.
CUNNINGHAM TOWER
Goshen, Connecticut
ABOUT THE HIKE
Mere feet from the parking lot along Toumey Road, the eerie ruins of Cunningham Tower is an intriguing site for explorers. Constructed in 1915 by Seymour Cunningham, the two-story tower is now little more than an open shell.
A detailed history of the site can be found on the Cornwall Historical Society’s website.
Cunningham Tower is far from the only noteworthy attraction in Mohawk Mountain State Forest. A short hike and an even shorter drive leads to a stunning overlook with picnic tables and spots to grill. A ski area operates seasonally off Great Hollow Road.
DISTANCE: Less than 0.1 miles
LEVEL OF DIFFICULTY: Easy
PARKING
There are numerous trails and places to park at Mohawk State Forest. The closet parking to Cunningham Tower is a small lot on Toumey Road in Goshen.
CASTLE CRAIG
Meriden, Connecticut
ABOUT THE HIKE
There is an extensive network of trails in Hubbard Park that offer numerous routes to the breathtaking vistas in the the Hanging Hills. Built atop the trap rock on East Peak, Castle Craig is the crown jewel of the 1,800 acre park in Meriden, Connecticut.
Many visitors to the park opt for the path with the most gradual incline, Reservoir Ave. The paved road is just over 6 miles up and back from the parking lot to the castle. I prefer to take the white trail, passing over the highway through a through a chainlink covered bridge and up a steep hill to the tower.
While the views from the top of the tower are incredible, there are a few things to keep in mind when making the trek. The loose stones along many parts of the trail can make the hike difficult to navigate and a bit treacherous for people with weak ankles. Be particularly mindful of your footing on the decent.
Due to the number of different trails, I strongly advise using a GPS or an app like All Trails to avoid getting lost. The routes to Castle Craig are delineated by castle shaped trail markers on the trees along the trail.
A detailed description of the trails and points of interest in Hubbard Park can be found on the Meriden Parks and Recreation website here.
DISTANCE: Approx 2.3 miles
LEVEL OF DIFFICULTY: Moderate / Difficult
PARKING
There are numerous trails at Hubbard Park. Castle Craig can be accessed by all of them, but parking to the most direct routes are inside Hubbard Park at the first corner of Mirror Lake Drive and the parking lot at the corner of Notch Road and Mirror Lake Drive.
If you’re not up for the hike, the road to Castle Craig is open May through October from 10:00 AM to 5:30 PM. Be sure to get beyond the gate before it closes and locks!
MOUNT TOM TOWER
Washington Depot, Connecticut
ABOUT THE HIKE
Mount Tom is a one of the oldest state parks in Connecticut. Nestled in the scenic Litchfield Hills region of the state, visitors to Mount Tom can enjoy swimming from a small beach, as well as fishing, picnicking and boating. The highlight of the park, however, is undoubtedly the stone lookout tower.
Take one of two trailheads for the yellow loop up a moderately steep hill. The ruins of an old chimney can be found at the beginning or the end of the hike, depending on where you start. After about a half mile, the trail opens up to Mount Tom Tower. Climb to the top for amazing 360 degree views.
DISTANCE: 1.3 miles
LEVEL OF DIFFICULTY: Easy / Moderate
PARKING
Mount Tom has several areas to park. All of them are a short walk to the trails that lead to the tower. After entering the state park onto Mount Tom Road in New Preston, continue past Camp Chinqueka towards the beach.
FORT GRISWOLD MONUMENT
Groton, Connecticut
ABOUT THE SITE
The Fort Griswold Monument was built between 1826 and 1830 to honor those who fought at the Battle of Groton Heights.
On September 6, 1781, General Benedict Arnold commanded a group of 1,600 British soldiers who descended on Groton. The 165 militia and local volunteers led by Colonel William Ledyard were severely outnumbered. The entire battle lasted only 40 minutes and left 85 Americans dead, including Colonel Ledyard, 5 nearly dead, and 36 severely wounded.
Today, the site is now Fort Griswold State Park. In addition to the monument and Revolutionary War Fort, it also includes the Monument House Museum and the Ebenezer Avery House. The grounds are open year round for visitors to explore.
The Groton Monument is open seasonally between Memorial Day and Labor Day. The view from the top offers a unique view of the fort below, as well as New London, the Thames River and the Long Island Sound, but the 166 steps in a tight spiral staircase without windows is not for the faint of heart. If you’re claustrophobic like I am, think twice before making the climb. Having second thoughts? The scenery from down below is still incredible.
DISTANCE: 0.2 - 0.5 miles
LEVEL OF DIFFICULTY: Easy / moderate
PARKING
There is street parking for Fort Griswold Battlefield State Park on Smith Street and Monument Street. A small parking lot at the corner of Latham Street and Thames Street is a short walk from the park. A seasonal water taxi operated by the Thames River Heritage Park brings visitors from City Pier and Fort Trumbull State Park in New London to a dock at 301 Thames Street, blocks from Fort Griswold.
HAYSTACK MOUNTAIN TOWER
Norfolk, Connecticut
ABOUT THE HIKE
Haystack Mountain State Park is one of Connecticut’s most underrated attractions. Located in the historic district of Norfolk, a relatively short and easy hike brings visitors to a beautiful three-story tower. The structure was built in 1929 from locally quarried stone to replace a wooden tower from 1886 that had been destroyed by a storm.
DISTANCE: 0.8 miles
LEVEL OF DIFFICULTY: Easy / Moderate
PARKING
Parking is available next to the trailhead to the Haystack Mountain Tower. Follow the road up from the park’s entrance off North Street in Norfolk.
APPLE HILL OBSERVATION DECK
Morris, Connecticut
ABOUT THE HIKE
The smallest lookout on this list, there’s something quite endearing about the observation deck on Apple Hill. There are several trailheads from East Shore Road, but the shortest walk begins from a small lot close to Morris Town Beach.
DISTANCE: 1 mile
LEVEL OF DIFFICULTY: Easy
PARKING
A small lot slightly uphill from 147 East Shore Road in Morris is the best place to park to access the trail to Apple Hill.
SESSIONS WOODS OBSERVATION TOWER
Burlington, Connecticut
ABOUT THE HIKE
Sessions Woods Wildlife Management Area contains a small network of trails for hikers of all ages and experience levels. Take the Beaver Pond Trail (orange), to get to the unassuming observation tower. While it isn’t my favorite Connecticut lookout, Sessions Woods is a wonderful destination for nature lovers.
DISTANCE: 2.6 miles
LEVEL OF DIFFICULTY: Easy
PARKING
Sessions Woods Wildlife Management Area has a parking lot at 341 Milford Street in Burlington.
FOX HILL TOWER
Vernon, Connecticut
ABOUT THE TOWER
Fox Hill Tower was constructed by during the Great Depression by the Works Progress Administration (WPA) as a monument to local veterans.
PARKING
Street parking for Fox Hill Tower is available on Submit Road.
CRANBROOK TOWER
Guilford, Connecticut
ABOUT THE TOWER
Before planning a visit, please note that Cranbrook Tower is located on private property. The impressive 65-foot stone tower was originally built to supply water to the large estate of Abel Chittenden in Guilford.
PARKING
Cranbrook Tower is located on private property. Parking is available a short walk away around the Guilford Town Green.
SOLDIERS' MONUMENT
Winsted, Connecticut
ABOUT THE TOWER
Like several other towers on this list, the Soldiers' Monument was built to honor veterans. This monument recognizes those who served in the Civil War and was dedicated on September 11, 1890.
PARKING
Street parking is available for the Winchester Soldiers' Monument at 84 Crown Street in Winsted.
SLEEPING GIANT OBSERVATION TOWER
Hamden, Connecticut
ABOUT THE HIKE
There are miles and miles of trails within Sleeping Giant State Park, some of which are among the most challenging in Connecticut. The most direct route to the Observation Tower is from the large parking lot just inside the park’s borders.
The trail and the tower itself were constructed as part of the New Deal’s Works Progress Administration. It is listed on the National Register of Historic Places.
Sleeping Giant State Park is a popular attraction, so expect lots of other hikers on the trails.
DISTANCE: 3.1 miles
LEVEL OF DIFFICULTY: Moderate
PARKING
The large parking lot just inside the entrance to Sleeping Giant State Park off Mount Carmel Avenue in Hamden is the most convenient place to access the trail that leads to the observation tower. Sleeping Giant has numerous other lots and street parking a short walk from a large network of trails.
SOAPSTONE MOUNTAIN OBSERVATION TOWER
Somers, Connecticut
ABOUT THE HIKE
Soapstone Mountain was purchased by the state of Connecticut in the late 1920s to erect a fire tower. After falling into disrepair, a brand spankin’ new observation tower was rebuilt in 2019. The large observation deck allows visitors to comfortably enjoy the panoramic views of Shenipsit State Forest without feeling too crowded.
DISTANCE: 1.4 - 2.3 miles
LEVEL OF DIFFICULTY: Moderate
PARKING
The Shenipsit State Forest contains a large network of trails, but the best parking to hike to the observation tower is the lot at the park’s entrance at 263 Gulf Road in Somers.
HEUBLEIN TOWER
Simsbury, Connecticut
ABOUT THE HIKE
The Heublein Tower in Talcott Mountain State Park is only accessible to visitors on foot. A steep half mile trek opens up to the scenic ridge line on the Metacomet Trail. The impressive 165-foot-tall building was constructed to withstand 100 MPH winds. Guests are able to go inside the museum Friday – Monday from 10:00 AM to 4:00 PM. Walk up to the top for a stunning 360 degree view!
For a more detailed history of the Heublein Tower, visit the Friends of the Heublein Tower’s website.
DISTANCE: 4 miles
LEVEL OF DIFFICULTY: Moderate / Difficult
PARKING
The most convenient parking to take the trails up to the Heublein Tower is the lot on Summit Ridge Drive in Simsbury.
SOUTHFORD FALLS FIRE TOWER
Southbury, Connecticut
ABOUT THE HIKE
Southford Falls is an idyllic state park in Southbury, Connecticut. Once the site of the Diamond Match Company, visitors today enjoy Southford Falls for its hiking trails, picnic area and trout fishing. A covered bridge and waterfall are mere feet from the parking lot.
Take the red trail to reach the fire tower. Not the most impressive tower or view point on this list, it’s still worth visiting for the other points of interest at Southford Falls State Park.
DISTANCE: 1.7 miles
LEVEL OF DIFFICULTY: Easy
PARKING
Southford Falls State Park has a parking lot at 175 Quaker Farms Road in Southbury.
