Things To Do In Guilford, CT

Nestled along the scenic shores of Long Island Sound, Guilford, Connecticut, is a charming coastal town that offers a delightful blend of history and natural beauty. This town has something for every visitor. From shopping and dining in the historic district to enjoying outdoor adventures, and even historic houses to tour, this charming little town is sure to become a favorite.

A historic red wooden house with a steep roof, symmetrical windows, and a central chimney, surrounded by green trees under a clear blue sky. — Photo credit: Kailey MarcAurele.

Jacob’s Beach

A peaceful beach scene with calm waters, overcast sky, shoreline with rocks, and distant houses on the right. — Photo credit: Kailey MarcAurele.

Jacob’s beach is a must-visit if you’re looking to enjoy the shoreline while you’re in Guilford. This park not only has a beautiful beach, but it also has amenities as well as a playground. It’s the perfect spot to spend a summer day, but it’s also super peaceful in the off-season.

Henry Whitfield State Museum

A historic stone house with a steep roof and small windows, surrounded by trees and a stone wall under a clear blue sky. — Image Credit: Image credit goes to.

Built in 1638, this house is considered to be Connecticut’s oldest house and the oldest stone house in New England. You’re able to tour inside of the house as well as explore some other buildings on the property. This is a great spot to visit if you’re interested in history and historic homes!

Bishops Orchards

Close-up of a scoop of cookies and cream ice cream on a waffle cone, with a blurred menu board in the background. — Photo credit: Kailey MarcAurele.

There’s plenty to do during a visit to Bishop Orchards year-round. There’s a farmers market, a winery, a creamery, and various opportunities to pick your own fruit! This is a great spot for a family day.

The Thomas Griswold House Museum

A white, two-story colonial-style house with a wooden roof, surrounded by trees and a small hedge in front. — Photo credit: Kailey MarcAurele.

Open seasonally, the Thomas Griswold House Museum is a historic house that is owned and run by the Guilford Keeping Society. This house, built in 1764, is a classic New England saltbox house. Take the guided tour to see the inside of the house and to learn a bit about the house’s history.

Guilford Town Boat Launch

A small, red wooden shed stands on a sandy beach with lush green trees in the background under a bright blue sky. — Image credit: Kailey MarcAurele.

Located at the mouth of the East River, this is a great spot to enjoy more coastal views that Guilford has to offer. This is also the best spot to see the Grass Island Shack. The Grass Island Shack was built in 1914 as a summer cottage on the west shore of Grass Island by a local druggist named J. Harrison Monroe. This is an iconic landmark in Guilford, Connecticut became the second most painted and photographed building on the East Coast.

The Hyland House Museum

The Hyland House is a beautiful historic house museum to visit just outside of the center of town. This house was built in 1713 and it’s even on the National Registry of Historic Places. The house offers guided tours, events, hands-on programs, classes, and research.

Guilford Town Green

Two-story white house with green shutters, a central entrance with a pediment, and tall bushes in front. Shadows from trees are cast on the building's facade. — Photo credit: Kailey MarcAurele

The Guilford Town Green has been the center of town since settlers came to the area. The green is surrounded by beautiful historic buildings and it’s has always been a center of town activity. Today, it’s an area where you can enjoy the green space as well as shop and dine in the buildings around the green.

Dudley Farm

A historic white two-story house surrounded by trees, with a porch and an American flag. A sign in front notes its placement on the National Register of Historic Places. — Image Credit: Image credit goes to.

This charming, historic farmhouse gives visitors a view into life in the late 19th century. In addition to touring the farmhouse, you can also explore the barns and our buildings. Inside some of these buildings are displays of old tools and farm equipment. It is a unique spot to visit if you’re into history.

Bluff Head Preserve

Aerial view of a small lake surrounded by trees and sparsely populated houses on a clear day. — Photo credit: Kailey MarcAurele.

This trail located in North Guilford offers some seriously beautiful views. Take the short hike to the overlook that offers great views of Myer Huber Pond below. The hike is just under two miles with 357 feet of elevation gain.

Chaffinch Island Park

Rocky shoreline with moss-covered rocks leading into a calm, overcast sea. Distant rocks and cloudy sky complete the scene. — Photo credit: Kailey MarcAurele.

This park offers views of the mouth of West River, Guildford Harbor, and Faulkner’s Island. There are benches to sit back and enjoy the views as well as a picnic area. This is also a popular spot to go crabbing and fishing.