Things To Do In Essex CT: Top 23 Most Unique Spots | Stanton House Inn

Essex Steam Train & Riverboat

Essex, Connecticut, gained the moniker, “the Perfect Small American Town” in the book 1000 Places to See Before You Die. This coastal village nestles along the Connecticut River, exuding charm at every corner. You might recognize it from Hallmark Christmas movies. Even the Travel Channel hailed it as the “most charming small town in Connecticut.” This writer is a fan, too. So this guide exists to navigate you through the best of Essex, CT. From steam train rides to art galleries, and from delectable eateries to scenic beauty, Essex has plenty of ways to experience the New England charm. It’s the ideal destination for a picturesque and charming retreat.


Ready to explore the best things to do in Essex, CT? Let’s get into it:


Quick hits

  • Take a journey through Essex, CT’s rich history and beautiful scenery. Enjoy activities such as the Steam Train & Riverboat journey and visits to local art galleries.
  • Indulge in delicious food at the Griswold Inn or Truffle Shots and perfect your swing at the Golf Center.
  • Stay overnight in one of many cozy inns or luxury hotels for a warm New England experience!

things to do in essex ct map Things to do in Essex CT: Top 23 Most Unique Spots
Map design by Stanton House Inn

A Brief History of Essex, Connecticut

Each building on Main Street counts as historic sites, in this writer's opinion

Essex was once a part of Saybrook, carrying the name Potapaug Quarter. It wasn’t until 1852 that it became its own entity. The town is famous for building Connecticut’s first battleship, the Oliver Cromwell, in 1774. That said, it’s most famous for the British raid during the War of 1812, which resulted in the burning of twenty-eight ships in the harbor.


The Worst Day in the History of Essex

Essex, once a major center of shipping and shipbuilding, was under a blockade by the British. Captain Richard Hayden had advertised his Black Prince as an ideal privateer. It’s likely what caught the attention of the British.


On April 8, 1814, approximately 136 British marines and sailors, under the command of Richard Coote, attacked Potopaug. They rowed six boats from four British warships anchored in Long Island Sound. The raiders journeyed 6 miles up the Connecticut River, bypassing the unmanned fort in Old Saybrook. Armed with an array of weapons, they responded to the single cannon fired by the town’s surprised defenders with a massive volley. Remarkably, neither side suffered casualties.


The British then marched to the Bushnell Tavern, now known as the Griswold Inn. They seized the town’s stores of rope and rum, valued at $100,000 or more. But their main targets were the newly constructed privateers in the harbor. Within 6 hours, they had set fire to the ships. They left downstream with two captured ships, including the Black Prince, a vessel that may have instigated the raid.


After the Revolutionary War

Shortly after the raid, the town changed its name to Essex.


Since 1964, the “Sailing Masters of 1812” of Essex have been commemorating the “Burning of the Ships”. Every second Saturday of May, they host an ancient fife and drum corps parade down Main Street, followed by a ceremony at the steamboat dock.


The Best Things to Do in Essex CT

The 1846 Baptist Church on Prospect Street is one of only three Egyptian Revival-style churches in the United States.

Essex offers a wealth of history and stunning landscapes in a small town. It’s an ideal spot for a weekend getaway or a relaxing CT day trip. Some of the attractions you can enjoy include the Essex Steam Train & Riverboat and the Connecticut River Museum. The charming downtown area is perfect for a leisurely stroll, with art galleries to explore and delightful eateries to try.


Experience the Essex Steam Train & Riverboat

Get ready for a unique journey aboard the Essex Steam Train & Riverboat. This adventure takes you through the picturesque Connecticut River Valley. The historic train and riverboat ride provide breathtaking views and a peek into the past. With a range of class experiences and special events such as the Essex Clipper Dinner Train, there’s plenty to enjoy.


The train ride is an experience in itself from Essex Station. It takes you through charming small towns and beautiful landscapes. Upon reaching the Haddam Swing Bridge, you’ll transition to a riverboat tour. Here, you can admire the stunning views of Gillette Castle State Park and the Long Island Sound. This is a fantastic opportunity to explore Essex and its surrounding areas in a unique and stylish way!


Stroll Through the Charming Historic Essex Village

The charming downtown of Essex, Connecticut, with its historic homes and shops

Why not enjoy a leisurely stroll through the quaint town of Essex? Historic buildings, charming boutiques, and tempting eateries line the picturesque Main Street.


Essex Village, previously known as Potapoug Point until 1854, was a busy shipbuilding center during the Revolutionary War and Civil War. A major boom in home construction took place between 1790 and 1820, with a preference for Federal architecture. The Hayden family built or inhabited the first eight structures on Main Street, including the famous Griswold Inn. Just south of these buildings was the Hayden Shipyard, hence the uniformity of architectural styles.


The Ebenezer Hayden House was the first hip-roof house in the lower Connecticut River Valley. The current Episcopal Church Rectory was the first brick house in the region. Federal style houses line Pratt Street, which runs parallel to Main Street. Their roof lines are perpendicular to the street, so more homes could be built on a given stretch of road. Two homes on Pratt Street feature Palladian windows in the garret area.


The 1846 Baptist Church on Prospect Street is one of only three Egyptian Revival-style churches in the United States.


Essex Marina from Essex Park

Essex Park

Essex Park is a charming little spot, just off Main Street. It boasts a gazebo providing shade and picturesque views of the river. It’s an ideal location for a picnic with some local takeout. Despite its small size, it’s worth a visit.


Connecticut River Museum

The Connecticut River Museum in Essex, Connecticut, showcasing the maritime history of the area

The Connecticut River Museum, located in the historic village of Essex, is as a hub for Connecticut River artisans. It is a trove of maritime heritage. The museum celebrates the history of the Connecticut River. It features interactive exhibits, a boardwalk, and a variety of educational programs.


A highlight of the museum is the chance to take a boat tour aboard the Onrust. This vessel is a replica of the first U.S. yacht, which was built in 1614. You can also:


  • Explore the Winter Wildlife boat tour and witness the river up close
  • Take a stroll through the museum itself, admiring the exhibits
  • See the working replica of the first American submarine, Turtle


Pratt House

If you’re a history enthusiast or an architecture buff, the Pratt House in Essex, CT is a must-visit. This house museum, exceptionally preserved, spans over two centuries of history. It offers docent-led tours and features period furniture. As you meander through the rooms, you’ll be wrapped in a charming atmosphere and marvel at the meticulous attention to detail. A trip to the Pratt House provides a delightful opportunity to delve deeper into Essex’s rich history.


Canfield Meadow Woods

Canfield Meadow Woods is quite a sight. It spans over 200 acres with 17 walking and hiking trails. This nature preserve is home to wetlands, wildlife, and scenic overlooks.


The trails are particularly special. Most of them take you through the woods, providing a cool, shady path on hot summer days. In the fall, these woods transform into a spectacle of vibrant foliage.


Don’t underestimate the trails. Some sections are steeply inclined. It’s wise to wear sturdy hiking shoes for your journey.


Ivoryton, Connecticut

The Gingerbread House of Ivoryton, in Essex, CT

Ivoryton is a small village, part of the town of Essex. It’s just a quick 10-minute drive from downtown Essex.


Once upon a time, Ivoryton was a bustling hub for wooden sailing ships. That focus shifted dramatically with the rise of the ivory and piano parts industry. The company spearheading this change was Comstock, Cheney & Co., a major producer of ivory products. Ivoryton became the economic heart of Essex and the lower Connecticut River Valley.


After the Civil War, Ivoryton experienced a housing boom. Particularly noteworthy were the houses on Victorian Row on East Main Street. The 1855 “Gingerbread House” and Parker House on North Main Street are especially impressive. These homes were owned by executives or stockholders of Comstock, Cheney & Co.


The most significant cultural shift, however, occurred between 1890 and 1920. The factory was in dire need of low-cost labor. To meet this demand, they brought in immigrants from Italy and Poland. These immigrants built homes, many of which still stand today. Although most of these homes have undergone substantial alterations, they’re still a reminder of those who worked for Comstock, Cheney & Co.


The Ivoryton Playhouse

You’ll also stumble upon a historical gem in Ivoryton – the Ivoryton Playhouse.


This playhouse is a piece of history, listed on the National Register of Historic Places. It’s also the country’s first continuously-operating summer theatre. Big names have graced its stage. Think Groucho Marx, Betty Grable, Talullah Bankhead, and Marlon Brando.


The playhouse runs from April through October. This extended season gives you plenty of opportunities to catch a show. It’s one of the best things to do in Essex, CT, at night.


Perfect Your Swing at Essex Indoor Golf Center

Golf clubs at the Essex Indoor Golf Center

For golf enthusiasts or those wanting to try something new, the Essex Indoor Golf Center is an ideal spot. This exciting indoor golfing experience boasts six large-screen simulator bays. Here, you can practice your swing or play on over 70 world-class courses.


The center offers:


  • Mini-golf virtual games
  • Simulated beer pong
  • Corn holes
  • Darts
  • Ski ball


Annual Events & Festivals in Essex, CT

Fireworks on the river from downtown Essex

In case you need another excuse to visit Essex, CT, the town hosts events year-round.


The Spring Boat Show is one of the must-visit spring festivals in CT. It’s an occasion where yachts and sailboats are on display for everyone to appreciate.


When October arrives in CT, Ivoryton hosts the Village Pumpkin Festival. It’s an event that features pumpkin carving, live music, and a haunted library. There are also activities like face painting and cookie decorating. There’s a selfie station and a parade too. People are encouraged to wear costumes and participate in the festivities.


In December, the Ivoryton Illumination event takes place. The village is decorated with over 500,000 lights. During the first weekend, there are special events. Santa pays a visit, people go caroling, and there are scavenger hunts. The town tree is lit up as well. The lights remain up throughout December, making it a great activity during December in Connecticut.


Shopping in Essex, Connecticut

Essex, CT hosts a variety of boutique shops and restaurants. You Me and the Sea offers cozy sweatshirts and sea glass jewelry, while J.Alden Clothiers offers fine clothing and furnishings.


The Cooper & Smith Gallery is a platform for contemporary fine art, featuring works by acclaimed local artists. The gallery hosts various art exhibitions and events throughout the year in its 5000 square feet of exhibition space.


Chocolate Geeks, an award-winning chocolatier, is a must-visit destination for their famous truffle shots in a sealed shot glass. Chocolate Geeks design these truffle shots with the center of the chocolate truffle in mind, with a silky filling made in small batches using only the best ingredients. They come in a variety of unique flavors like Whisky Caramel and Fig + Balsamic, as well as classics.


Restaurants in Essex, CT

Delicious seafood and great food in no particular order at Scotch Plains Tavern

Essex, CT, hosts a diverse culinary scene. Some of the best restaurants in town showcase the remarkable flavors and culinary talents of Essex, CT.


First things first, let’s talk about coffee. Essex Coffee & Tea Company is a humble, independent establishment. They offer gourmet coffee, organic loose leaf tea, and fresh baked goods. They’re a supporter of local artisans, showcasing their work with monthly displays. It’s a great stop for breakfast in Essex, CT.


Scotch Plains Tavern offers an eclectic/American menu, great drinks, and a local beer list. Olive Oyl’s Carry Out Cuisine is perfect for on-the-go dining, perfect for picnics or afternoon drives. Their menu includes fresh salads, hearty sandwiches, and daily specials.


The historic Griswold Inn is on the appropriately named Griswold Square. Famous for its cozy atmosphere since 1776, hosts a variety of dining options, including a tavern and wine bar. It offers classic American cuisine with a warm, inviting atmosphere and a seasonal menu created by award-winning Executive Chef Toppin. The famous buffet-style Hunt Breakfast on Sunday mornings is a must-try.


And finish-off with ice cream from Sweet P’s. Or head here for an afternoon treat. Sweet P’s, a family-owned and operated ice cream parlor, serves Ashley’s Premium Ice Cream.


Directions to Essex, CT, from Greenwich, CT

Planning a trip from Greenwich, CT to Essex, CT? You’re in luck! The trip from our Greenwich, CT, bed and breakfast offers a scenic drive through some of the Connecticut shoreline’s most charming towns. Whether you opt to take the fastest route via the I-95 N or the Merritt Parkway, you’re in for a pleasant drive. New Haven is a great stop along the way, especially for lunch or dinner on the way back.


Hotels, Inns, and Places to Stay in Essex, Connecticut

Dinner train welcoming travelers to one of the top attractions on Main St

If you’d rather spend more than a day in Essex and nearby, it’s also a great spot for weekend getaways in CT. A few of the most unique options among the list of hotels, inns, and places to stay in Essex, CT, include:


The Griswold Inn

The Griswold Inn, often referred to as “the Gris,” is a historic landmark. Having opened its doors in 1776, it’s one of the oldest continuously operating inns in America. A unique charm and warmth exudes from what is one of the most historic inns in CT. Nestled on Main Street in Essex Village, it’s perfectly positioned for a weekend getaway. A variety of dining options and a general store are within easy reach. The rooms are tastefully decorated in a classic New England style. The Griswold Inn features a top-rated tavern and wine bar. It’s a great place to stay at any time of year. That said, it becomes particularly cozy during the fall and winter, especially around Christmas. What’s more, it’s conveniently located right on Main Street.


The Copper Beech Inn

At the Copper Beech Inn, you’ll find 22 rooms and suites that promise luxurious comfort. These accommodations are spread across the Main House, the Carriage House, and the Comstock House. Each room is a tasteful blend of period antiques, oriental rugs, and richly textured fabrics. After a day of exploring the quaint villages of the Lower Connecticut River Valley, this inn serves as a perfect retreat. This Ivoryton, Connecticut, inn exudes traditional New England elegance. The restaurant at the Copper Beech Inn is also well-known for its chic sophistication and innovative cuisine.


More Towns and Cities to Explore Near Essex, CT

Marina on the water at sunset near the historic Essex village

Ready to keep exploring the Connecticut River Valley? Then read on for some more charming towns with their roster of unique CT attractions. Some of the absolute most unique spots here are the Florence Griswold Museum and Gillette Castle State Park.


Old Saybrook, CT

Just a short 15-minute drive from Essex, you’ll find Old Saybrook. This coastal town is rich in history, museums, and stunning scenery. It’s also home to Harvey Beach, the closest beach to Essex and one of the best beaches in CT.


Old Saybrook, Connecticut, gained fame as the home of Katherine Hepburn. Spend a day here and you’ll understand why. Explore the picturesque Main Street. Seek out views of Lynde Point Lighthouse, one of the most charming lighthouses in CT, along the shore. When it’s time to eat, you’ll find some amazing restaurants from which to choose.


Old Lyme, Connecticut

A short 20-minute drive from Essex, a visit to Old Lyme, CT, is worth every minute. Old Lyme is known far and wide for its artistic legacy and breathtaking coastal views. You’ve got the Florence Griswold Museum and the Lyme Art Association Gallery, both famous in their own right. And the historic district? Perfect for a slow, easy walk. For the great outdoors, Old Lyme’s beaches and trails are something to behold, especially Selden Neck State Park.


Chester, CT

Chester, Connecticut, is a small town brimming with charm. You’ll find one of the best breweries in CT there called Little House Brewing. It’s known for its top-notch beers and comfortable outdoor seating. For dessert, Honeycone Ice Cream offers a wide range of delightful flavors. When it comes to dining, Chester doesn’t disappoint. Otto serves delicious pizza, while Grano Arso is famed for its pasta. For classic American dishes with a beautiful view, head to The Brushmill by the Waterfall. With its picturesque scenery and excellent dining options, Chester is the perfect destination for a leisurely afternoon.


East Haddam, Connecticut

East Haddam, Connecticut, is a small town that’s just a 20-minute drive from Essex and is well worth exploring. The town is home to the historic Gillette Castle, a hilltop fortress once owned by a wealthy eccentric. This site is one of the most unique attractions in CT. The castle was chosen by its original owner, actor William Gillette, for its stunning views of the Connecticut River. Another notable site in East Haddam is the Goodspeed Opera House. This beautifully restored Victorian building hosts high-caliber musical performances. With its rich history, vibrant culture, and scenic beauty, East Haddam makes for an ideal day trip from Essex.



Often referred to as “the Perfect Small American Town,” Essex, Connecticut, is a treasure trove of attractions for visitors. You can embark on a historic journey with the Essex Steam Train & Riverboat or delve into the past at the Connecticut River Museum. The small town boasts a charming downtown area, ideal for a leisurely stroll. It’s dotted with art galleries waiting to be explored and delightful eateries begging to be tried. Among these, the historic Griswold Inn and the innovative Copper Beech Inn stand out. Essex also hosts a variety of boutique shops and organizes events throughout the year. There’s never a bad reason to pop over to Essex.


Frequently Asked Questions


Is Essex CT worth visiting?

Essex CT is an amazing place to visit, with plenty of shops, historic homes, a popular and historic inn, eateries and stunning scenery.


What is Essex CT known for?

Essex CT, known for its captivating downtown area and Main Street, is a sight to behold. The town’s charm is enhanced by scenic landscapes, majestic trees and gardens, and fascinating architecture. It is recognized for its historic district, which proudly sits on the National Register of Historic Places. As you stroll through the town, you’ll find beautiful Federal, Victorian, and Cape Cod-style houses lining the streets. Essex is more than just a great place to live and work – it’s a delightful destination to visit. The town offers a variety of shops, restaurants, and attractions. It also boasts a vibrant arts and culture scene. Whether you’re seeking tranquility or adventure, Essex CT has something for everyone.


Is Essex CT a good place to retire?

Located in Middlesex County, Essex is an ideal retirement destination. This area offers residents a wealth of recreational opportunities, including a historic playhouse, libraries, and museums. Dining options are plentiful with a variety of restaurants and tap rooms. The public schools in Essex are highly rated, making it a great place for families as well. The town has a suburban feel and a liberal-leaning community.


What are some must-visit attractions in Essex, CT?

For a unique experience in Essex, CT, several attractions are a must-visit. These include the Essex Steam Train & Riverboat, the Connecticut River Museum, and the Pratt House. Also, don’t miss out on the Cooper & Smith Gallery.


What types of accommodations are available in Essex, CT?

Essex, CT, boasts a variety of accommodations, ranging from historic inns to modern hotels. One such place is The Griswold Inn. Another notable accommodation is The Copper Beech Inn. For nearby chain hotels and resorts, Old Saybrook, CT, is home to the Quality Inn, Super 8 by Wyndham, and Saybrook Point Inn & Spa.


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