If you’re looking for a picturesque and charming small town in Connecticut for your next getaway, Essex is going to fit the bill perfectly. Located along the Connecticut River, this cute little town has charm at every corner. In fact, it’s so postcard-worthy, that some Hallmark Christmas movies have filmed here, and the Travel Channel called it the “most charming small town in Connecticut.”
Have I convinced you? 🙂 Hopefully I have.
In this post, I’m here to help you plan the perfect getaway by sharing all the best things to do in Essex, CT. With that, let’s get started.
Is Essex, CT Worth Visiting?
Oh, absolutely! Not only is the Griswold Inn one of the coziest places to stay in Connecticut, the town itself truly feels like a movie set. The Main Street shops and restaurants are lovely, the architecture and houses are postcard-ready, and there are plenty of amazing sites and attractions nearby to fill your time (you know, when you’re not admiring the scenery downtown).
Best Things To Do In Essex, CT
In no particular order, here are my suggestions for the best things to do in Essex, CT!
1. Stroll The Charming Essex Village Main Street
One of the best parts of Essex Village is the incredibly charming downtown and Main Street. Lined with shops, historic homes, a popular inn, eateries and beautiful scenery, it’ll be hard to forget you’re in one of the best small towns in Connecticut. This is definitely a must-see during your visit (and kind of hard to miss).
For shopping, I recommend strolling the entire area, but some of my favorite shops are Essex Mercantile, Connecticut River Artisans, Emmy’s On Main, and Goods & Curiosities (part of the Griswold Inn). If you’re visiting with kids, you’ll also want to explore Toys Ahoy!
For a coffee, I recommend popping into Essex Coffee and Tea Company, but they also have great baked goods and a variety of beverages to choose from.
2. Explore The Essex Steam Train & Riverboat Museum
One of the top attractions in Essex is the Essex Steam Train & Riverboat Museum, and this is an adventure you’ll definitely want to have on your radar as you plan your itinerary.
With an authentic steam-powered train and gorgeous river boat, visitors can tailor a tour through the Connecticut River Valley to their preferences. Tour options include a combined steam-train and riverboat combination tour, just a train or riverboat tour, and even a dinner train experience.
During your train ride, you’ll pass by state parks, wetlands, natural birding habitats and scenic coves that are difficult to see unless you have a boat (or a train!). During river boat cruises, you’ll take in views of marshes and more wildlife, Gillette Castle, and Haddam Swing Bridge (plus lots more, of course).
3. Book A Cozy Stay At The Griswold Inn
The Griswold Inn is one of the best and most cozy places to stay in all of Connecticut, and it just so happens to be in a perfect location right on Main Street in Essex Village. When you check-in for your stay at Griswold Inn, you’ll feel like you’ve stepped back in time in the best possible way.
Home to a few dining options and general store, it makes it easy to plan a wonderful weekend getaway when you stay here. Rooms at the inn are decorated with a welcoming, traditional New England-style, and the tavern and wine bar here are some of the top-rated places in Essex.
And of course, you’re just steps from everything Main Street has to offer!
While The Griswold Inn is perfect year-round, it’s especially cozy in the fall and winter, especially during the Christmas season.
4. Get Some Truffle Shots At Chocolate Geeks
Essex is home to award-winning chocolatiers, and one place you don’t want to skip is Chocolate Geeks to try one of their famous truffle shots.
Truffle shots were designs with the best part of the chocolate truffle in mind – the center. That silky filling is made is small batches using only the best ingredients, and then poured into a shot glass for you to enjoy. And not only are these incredible chocolates, they come in a variety of unique flavors like Whisky Caramel and Fig + Balsamic (but don’t worry, they have the classics, too!).
Not only will you find the truffle shots here, you can also buy some pretty amazing cookies and craft chocolate bars.
5. Take In A Show At The Ivoryton Playhouse
Ivoryton is a village in the town of Essex, and only about a 10-minute drive from downtown Essex you’ll find the amazing Ivoryton Playhouse.
This venue is listed on the National Register of Historic Places, and is regarded as the country’s first continually-operating summer theatre. It’s even had notable performers like Groucho Marx, Betty Grable, Talullah Bankhead, and Marlon Brando grace the stage!
Performances at the playhouse typically run April through October, so the season is pretty long for a summer venue, and there are so many opportunities for a night at the theater. This is definitely one of the best things to do in Essex in the evenings.
6. Visit The Connecticut River Museum & Set Sail On Onrust
So much history has taken place along the Connecticut River region, and this museum does an incredible job showcasing all the interesting stories from the past. Sitting right along the river, not only are the water view lovely, the museum has exhibits on the Native American history on the river, the local ecosystem, and a great mix of rotating exhibits.
The museum also hosts public charters on two vessels: The Onrust and RiverQuest. The Onrust is a unique experience because the vessel is a replica of the first U.S. yacht, originally built in 1614. Cruises on the Onrust take place in afternoons and during sunset seasonally, and also include admission to the museum.
For a slightly different experience, you can hop aboard RiverQuest, which sets off onto the river for amazing wildlife cruises.
7. Enjoy The Views At Essex Park
Essex Park is just off Main Street, and is such a beautiful little spot in town. With a nice gazebo that offers some shade, and views of the river, it’s the perfect spot to grab some takeout and have a picnic in town. While it’s small, it’s so easy to swing by, so definitely don’t skip it.
8. Get An Ice Cream At Sweet P’s
The best place in town for ice cream is definitely Sweet P’s, and since they serve Ashley’s Premium Ice Cream, you know it’s going to be good. Ashley’s is known around Connecticut as some of the best, and is made is only the best ingredients, which means every lick is perfection.
And Sweet P’s delivers when it comes to options and flavors. They offer all the classics, and also have some fun ones like Dulce De Leche, Espresso Bean, and Cookie Batter. Get a cup or a cone, but you ca also go for a sundae, banana split, strawberry shortcake, milkshake, and even an acai bowl!
9. Visit The Harbor
A couple of blocks from Main Street is the harbor in Essex, and while this is also small, it makes for a nice little walk when exploring the town.
This is the harbor where you pick up the Essex Island ferry (more on that next!), and it’s also home to the cute little Essex Reef Lighthouse. There are some nice photo spots along the harbor, and is worth a quick walk over to check it out.
10. Ride The Ferry To Essex Island Marina
While in Essex Village, you can hop on the Essex Island Marina ferry and explore a 13-acre island with fun amenities!
The seasonal ferry to the island takes less than a minute, and it’s free to ride. Once you arrive on the island, you’ll find a restaurant, a pool, a dog park, BBQ grills, lawn games and a playground for kids. This is another awesome place to pack up a picnic, enjoy the natural scenery, and spend the afternoon outdoors.
11. Hit The Trails At Canfield Meadow Woods
The Canfield Meadow Woods is a wonderful nature preserve, spanning over 200 acres, and filled with 17 walking and hiking trails, wetlands, wildlife, scenic overlooks and more.
What I love about this preserve is that most of the trails take you through the woods, which offers shade from the sun on warmer summer days, and during the fall, it’s filled with gorgeous foliage.
Pro Tip: The trails through the preserve are generally easy, but there are some steeper inclines, so it’s a good idea to come prepared with sturdy hiking shoes.
12. Get A Hole In One At The Essex Indoor Golf Center
If you happen to have a rainy day during your trip to Essex, one of the fun indoor things to do is spend a few hours at the Golf Center. This entirely indoor experience had 6 large-screen simulator bays that are so accurate, they’ve been approved by the PGA!
Once you’re settled in, you can choose to play a round from over 70 international courses, have fun with fantasy mini-golf games, or even play simulated beer pong, corn holes, darts and ski ball. So really, the entire experience is awesome for both pro golfers and families with children.
Not only do they offer a unique golfing experience, they also have an awesome food and drink selection at their on-site eatery, perfectly named The Grumpy Caddy. Have some drinks and snacks delivered to your bay for the ultimate afternoon of indoor golfing.
13. Celebrate Fall With The Village Pumpkin Festival
If you visit the area in the fall season, you’ll want to make a trip over to the village of Ivoryton to experience their Village Pumpkin Festival! Guaranteed to put you in the fall spirit, the Pumpkin Festival takes place every October, and is packed with festive scenery and even better events. Whether you just walk around to enjoy the festivities as an observer, or join in on the fun, it’s always a good time!
During the festival, you’ll find pumpkin carving, live music, a haunted library, face painting, cookie decorating, a selfie station, parade, and so much more. Oh, and costumes are highly encouraged!
14. Enjoy The Christmas Lights In December
Continuing with seasonal celebrations, the Ivoryton Illumination event in December for the holidays is also one you’ll want to experience. During this event, over 500,000 lights are hung throughout the village, and the first weekend in December brings special events to kick off the holidays, like a visit from Santa, caroling, scavenger hunts, and the main event, the town tree lighting.
But don’t worry, if you can’t visit that weekend, the lights stay up through December, making it magical all month long.
Things To Do Near Essex, CT
I think I’ve mentioned (maybe too many times 😉) how cute Essex is, but there are also some awesome things to do just outside of town that are definitely worth your time. Here are the things I recommend checking out that are very close to Essex.
15. Visit Gillette Castle State Park
One of the top attractions in the Connecticut River Valley is Gillette Castle State Park, and this is also one of the coolest things to do in the entire state. And since it’s only about 30 minutes from Essex Village, it’s so easy to visit when you’re in the area.
Built in 1919 by actor William Hooker Gillette, the castle sits atop a hill overlooking the river and valley, and looks like a true medieval castle you’d find in Europe. Tours are given inside the castle seasonally from late-May through Labor Day weekend, but the grounds are open year-round. The castle is such a cool thing the experience, so I definitely recommend doing the tour.
The grounds and trails around the castle are also worth exploring, and you’ll find facilities like food concessions, bathrooms, and a picnic shelter on-site.
16. Hike To Castle Craig
Yep, you can see not one, but two castles near Essex! A bit further away than Gillette Castle is Castle Craig, which is about an hour from Essex. This castle requires a scenic 3-mile hike (round trip), but is such a fun and unique thing to do in the area.
The castle itself is more of a tower than anything, but the views are what makes it worth the effort. This is also an incredible spot in the fall for foliage color!
17. Enjoy The Coast At Hammonasset Beach State Park
The best beach near Essex can be found at Hammonasset Beach State Park, which is less than 30 minutes from Essex Village.
This gorgeous 2-mile long stretch of sandy shoreline on Long Island Sound is perfect for a day at the beach. It’s also the longest beach in the state! And with facilities like food concessions, bathrooms and showers, you’ll have everything you need.
The beach is only part of this awesome state park, though, and you’ll also find nature trails, a nature center here, picnicking, and camping.
More Great Towns Near Essex, CT To Visit
Looking for even more things to do near Essex? I’ve got answers! Here are some lovely towns near Essex that make for great afternoon excursions or day trips.
The closest town to Essex that also feels like a postcard is the darling little town of Chester. While Chester is small, it’s perfect for an afternoon stroll, and is home to a great brewery, cute shops, awesome restaurants and adorable scenery.
Little House Brewing can be found right in town, and they make some pretty great beers! They also have a nice outdoor seating area in the front, and a great beer garden in the back.
Honeycone Ice Cream is another awesome place to check out, as they concoct some really awesome flavors, but also service up some of the classics.
The dining scene in Chester is also pretty great, and between Otto for pizza, Grano Arso for pasta, and the scenic The Brushmill by the Waterfall for classic American dishes, you can’t go wrong.
Another one of my favorite towns in Connecticut is Mystic, which sits along the Mystic River and offers a lot of fun things to do. With a charming Main Street, a very cool bascule bridge, the Mystic Seaport Museum with tall ships you can explore, great shopping, and the cute little Olde Mystik Village, you can definitely spend a whole day here.
20. Old Saybrook
A great little coastal town that’s only about 15 minutes from Essex is Old Saybrook, which is rich in history, museums and beautiful scenery. It also has the closest beach to Essex, which is Harvey Beach.
Made famous by being the home of Katherine Hepburn, some of the best things to do during a day trip here are explore the picturesque Main Street, look for views of Lynde Point Lighthouse along the shore, tour the Florence Griswold Museum, and dine at one of the amazing restaurants.
21. Westerly, RI
About 45 minutes from Essex is one of New England premier beach towns – Westerly, RI, which is just over the RI/CT border. With stunning coastline and beaches to explore, a wonderful downtown scene, a lighthouse, great beach bars and restaurants, parks, and so much more, you can easily spend an entire day here!
Here are some posts on these destinations you can check out:
Best Restaurants In Essex, CT
Wondering where to eat in Essex? I’ve got you covered. Here are some suggestions to check out while you plan your itinerary:
Griswold Inn – As mentioned before, this great little inn has a restaurant that’s been named the coziest restaurant in Connecticut, so you’ll definitely want to book a table here during your visit! There are a few options for dining, including a tavern and wine bar.
Carlson’s Landing – Riverfront dining with delicious seafood, awesome drinks and covered outdoor seating in a more upscale atmosphere.
Scotch Plains Tavern – A really fun place with an eclectic/American menu, great drinks and an awesome local beer list.
Olive Oyl’s Carry Out Cuisine – The perfect place to grab a salad or sandwich on-the-go to bring to the park, or before taking an afternoon drive.
Best Time Of Year To Visit Essex
Honestly, any time. Essex is a really great year-round destination, and does a wonderful job celebrating all the seasons. And since it’s not a huge beach destination, summer isn’t necessarily peak season, which is a nice respite from most of coastal New England (although, it’s great in the summer, too!).
During mid-late Spring, the streets will be lined with blooming trees, and the weather is often lovely, and then of course, fall is also fantastic because of the foliage and seasonal activities. And it’s going to be hard to resist Essex in December for all the Christmas festivities!
Does Essex, CT Make A Good Day Trip?
Yes! In fact, this is a great little town for a day trip in Connecticut. While it’s small, there’s still plenty to do to fill up an entire day, and this will allow you to explore at a slower and more relaxed pace.
What Movies Were Filmed In Essex, CT?
Two Hallmark Christmas movies have been filmed in Essex, CT, including Christmas at Pemberley Manor and Next Stop, Christmas. The Essex Steam Train was used in the Next Stop, Christmas movie, and the Griswold Inn, and parts of downtown Essex, where used in Christmas at Pemberley Manor.
The Netflix Christmas movie, The Noel Diary, was also filmed in Essex.
What Is Essex, CT Known For?
Essex is known for being a historic destination, with roots in the War of 1812, as well as building the Oliver Cromwell in 1774, the state’s first battleship.
In recent years, Essex has become famous for being one of Connecticut’s most charming and picturesque towns, due largely in part to the Griswold Inn being featured in a few Christmas movies.
The village of Ivoryton in Essex is also known for being a top Christmas destination in New England with their Ivoryton Illuminations display, which features over 500,000 lights around the village.
Does Essex, CT Have A Beach?
Essex, CT doesn’t have any beaches, however, there are plenty nearby! Harvey Beach in Old Saybrook is probably the closest, but it’s pretty small. The best nearby option is in Madison, CT at Hammonasset Beach State Park.
The next best option is to drive to Westerly, RI and explore the many beaches there.
More posts you may enjoy:
- Summer In Connecticut: The Best Things To Do!
- Incredible New England Resorts & Spas
- Best Beach Towns In New England
- Fun Day Trips In New England
That’s A Wrap On Things To Do In Essex, CT
Now that you know all the very best things to do in Essex, CT, you’re ready to plan the perfect getaway! Go ahead and book that room at the Griswold Inn, spend your afternoons on Main Street, and plan fun day trips to nearby areas. All of these things combined are going to make you feel as though you’ve stepped into a postcard for one of your most relaxing getaways in Connecticut yet.