Chasing Waterfalls: 3 Days Exploring Connecticut’s State Parks

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Connecticut may be small, but it’s packed with natural wonders to explore. From cascading waterfalls to dense forests and shimmering lakes, the state is home to some of the most beautiful and diverse landscapes in the Northeast. Whether you’re a seasoned hiker, a nature lover, or just looking to escape the city for a few days, Connecticut’s state parks and waterfalls offer a world of adventure and discovery.

Follow this three-day itinerary to help make the most of your time in Connecticut and experience the best of what the state has to offer.

Day 1 – Hike Southwestern Connecticut’s Sleeping Giant

Getting There

Tweed New Haven Regional Airport (HVN) is the closest option for those looking to travel from New Haven, Connecticut. It primarily offers regional flights to and from Philadelphia, Washington D.C., and Nantucket destinations.

Morning

Grab breakfast at Bella’s Cafe, a New Haven Staple for over 20 years. Sink your teeth into cinnamon-sugar French Toast, sizzling bacon, and fluffy scrambled eggs. Order some of their homemade baked goods for the road – the fresh scones are heavenly. 

Lookout tower, Sleeping Giant State Park, Hamden, CT. Photo Courtesy of Bob P.B.

After breakfast, enjoy a 20-minute scenic drive from New Haven along the Quinnipiac River to Sleeping Giant State Park in Hamden. Renowned for its striking two-mile-long mountaintop resembling a human figure lying in repose, the iconic “Sleeping Giant” is an alluring feature of Connecticut’s south-central skyline. The park’s observation tower, located at the summit of Mount Carmel, provides spectacular 360-degree panoramic views of the park and Long Island Sound.

Travel to the north side of the observation tower for views of the breathtaking Gorge Cascade Falls. With a dynamic 25-foot drop between the two falls, this impressive waterfall is the perfect spot for some Instagram-worthy photos.

Afternoon

After your hike, enjoy lunch at Eli’s on Whitney in Hamden. Eli’s offers casual American fare, such as burgers, hand-cut fries, and a unique selection of craft beer. From Eli’s, drive 30 minutes to Wadsworth Falls State Park in Middletown, which features the stunning namesake – Wadsworth Falls – and the historic Coginchaug River that winds along the park’s western boundary. You’ll find two waterfalls here, the Big and Little Falls. At Big Falls, the Coginchaug River cascades down 30 feet, while Little Falls flows from an outcrop of sandstone along Wadsworth Brook. You can easily access these falls by traversing one of the park’s trails.

If you need to cool off after your hike, the park has a swimming area for a quick dip.

Evening

After a full day of hiking, drive 30 minutes to Manchester and have dinner at Pastrami on Wry, a neat little sandwich shop with a sizeable craft beer menu. With a massive array of sandwiches, including vegetarian and gluten-free options, this cozy spot offers something for everyone. Don’t skip a delicious milkshake made with ice cream from a Manchester staple, Royal Ice Cream Co.

End the day by checking in at the Manchester Inn, just one mile from the restaurant. Located in the heart of Manchester, the Manchester Inn offers a cozy spot with no-frills amenities with easy access to shopping and dining.

Day 2 – Central Connecticut’s Cascading Falls and Winding Trails

Morning

Start your day with a handmade omelet or some ‘out of this world’ French Toast for breakfast at The Cosmic Omelet in Manchester. This space-themed eatery serves up classic breakfast favorites with a supernova twist.

Waterfalls in Enders State Forest in Granby, Connecticut.

Hit the road and drive to Enders State Forest in Granby. Spanning 2,098 acres, this spectacular forest is home to eight miles of trails that range from easy two-mile hikes to more challenging six-mile treks. But, of course, the star of the show is Enders Brook Falls, one of Connecticut’s most photographed spots. The 30-foot cascading waterfall is surrounded by rugged and rocky terrain and can be accessed via two moderate trails that lead to its base.

Afternoon

After spending the morning exploring falls, trails, and lookouts, head south to Newington and grab lunch at Rooster Co. This restaurant serves delectable American cuisine crafted from fresh, locally sourced ingredients such as the flavorful meatball salad, or the turkey melt with bacon and caramelized onions.

A sunset over a calm lake in Winding Trails, Farmington, Connecticut.

Your next adventure is a short drive to Winding Trails in Farmington. First, enjoy a stroll or a swim in the 80-acre Dunning Lake – visitors regularly flock here for summer activities such as swimming, fishing, boating, and picnicking. Next, 12.5 miles of hiking trails and waterfront paths will take you to Walton Pond and Nature’s Porch – a wildlife viewing area where you can often spot red foxes, wild turkeys and scrambling chipmunks. 

Evening

After a nature-filled day through central Connecticut, check in at the Courtyard Hartford Farmington. Or, for more elegant bed and breakfast-style accommodations, stay overnight at The Farmington Inn & Suites.

Day 3 – Immerse Yourself in the History & Nature of Eastern Connecticut

Morning

Start your day with an early morning road trip to Pomfret and grab breakfast at the Vanilla Bean Café, a 20-minute drive from the first park. Serving the town for over 30 years, you can enjoy freshly-baked goods, such as muffins, bagels, croissants, and cookies – perfect for packing as a snack between hikes.  

Mashamoquet Brook State Park, Pomfret. Connecticut. Photo Courtesy of J. Stephen Conn.

Up next is Mashamoquet Brook State Park. First, head to The Wolf Den, the most renowned attraction in this park and home to two fascinating geological formations: Table Rock and Indian Chair Stone, two large boulders shaped by centuries of erosion. Next, spend the morning hiking one of the many trails. The Stone Wall Trail is a short trek through a breathtaking wooded area to the park’s historic stone walls, or hike the Frog Rock Trail, which leads to a unique rock formation resembling a frog. Looking to cast a line? Rent a canoe or rowboat from the park office and try catching bass and pickerel at the Pomfret Reservoir.

Afternoon

Drive an hour south to East Haddam for an afternoon of adventures at Devil’s Hopyard State Park. Grab lunch on your way at Gelston House; the menu offers a wide array of cuisine such as crab cakes, fish tacos and sandwiches – if you’re feeling indulgent, order the short rib grilled cheese.

Chapman Falls, East Haddam, Connecticut, Devil’s Hopyard State Park.

Fueled up for the rest of the day, it’s time to head into the 860-acre park and see its star attraction – Chapman Falls, an over 60-foot waterfall that flows into the Eightmile River. Considered the most popular and picturesque waterfall in Connecticut, it’s also the most crowded, so plan accordingly. It’s recommended to visit in the late afternoon. Next, stroll along the Eightmile River, fed by several tributaries and home to silent pools and gentle rapids.

Evening

Wrap up your three-day journey with dinner in Old Saybrook. Liv’s Oyster Bar & Restaurant is a local favorite serving up fresh oysters at the raw bar and seafood favorites such as sesame-crusted tuna, fried shrimp and clam chowder. Then, rest up from the day at the Saybrook Point Resort & Marina, luxury accommodations with the stunning natural beauty of the Long Island Sound.

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