Tucked away along the Connecticut River Valley region, Chester is an idyllic little New England gem that makes for a wonderful day trip, or quiet getaway in the Nutmeg State. Here, you’ll find cobblestone streets, historic buildings, a colorful Main Street, wonderful boutiques, and an impressive dining scene. And this post is all about the absolute best things to do in Chester, CT to help you plan your itinerary!
Even though it’s a very small town that doesn’t take more than a day to experience, I love Chester because it forces you to slow down a bit, live in the moment, and enjoy what feels like an escape from reality. It’s also close by a lot of really great attractions in Connecticut, which I’ll also touch on more in the post.
With that, let’s get started!
Best Things To Do In Chester, CT
In no particular order, here are all the things that should be on your radar
when you plan a trip to this cute little town.
1. Enjoy The Charming Downtown
One of the biggest draws is most definitely the charming downtown, which is lined with independent shops and restaurants housed in colorful buildings. You won’t find any chains here, which makes the town even more inviting and magical.
A few of the can’t-miss shops you’ll want to check out are The Little Shop by Nora Murphy Country House, Lark and The Wayfinder Society. The shops in Chester are high-end for the most part, this is a great place of you’re looking for unique investment pieces (or even just a bit of inspiration!).
Main Street is also lined with quite a few restaurants, and a brewery, but more on that later in the post 🙂
2. Get An Ice Cream At Honeycone
Along Main Street, you’ll also find the adorable Honeycone ice cream shop, and this is a must during your visit! They make delicious, craft homemade ice cream here, and they introduce amazing seasonal flavors monthly. This is the place to go for creative flavors (but don’t worry, they have great classics, too).
Past seasonal flavors have included blueberry lemon curd, honey lavender, cider donut, sweet corn blueberry and gingerbread. They also make milkshakes and sundaes that are picture-worthy. I’m honestly so sad I don’t live closer because I literally want to try everything they make, so this is always one place I have to visit when I’m in Chester.
3. Grab A Pint A Little House Brewing
For such a small town, it come as a surprise that Chester has its own brewery! And, it’s actually really great. My husband is really into beers, and he absolutely loved it here. The location is also very convenient right in downtown Chester on Main Street.
They have a nice outdoor seating area in the front of the brewery, and two cozy outdoor seating areas out back. I highly suggest getting a flight during your visit to try a few of their brews, and definitely get the Chips & Dip sour. I will admit, it wasn’t my personal favorite, but my husband couldn’t stop raving about it. The flavor profiles are so unique that you just have to give it a go and see what you think for yourself.
My personal favorite here was the Coffee & Donuts, which is an Imperial Pastry Stout that’s brewed with jelly donuts, and it was amazing.
4. Book A Table At The Brushmill By The Waterfall
One of the most scenic restaurants in Chester is the Brushmill By The Waterfall, and just your walk from the parking lot to the restaurant is going to feel special because you have to go across the cute little covered bridge. And the experience only gets better from there.
The history of the restaurant’s building dates back to the 1800s when it was used as a grist, sawmill, and woodworking property, and much of the history has been preserved. While the restaurant feels fresh and modern, it also does a wonderful job paying homage to its roots.
There are two ways you can dine at the restaurant – in the fine dining space, or at the tavern. Both feature elevated food with a focus on fresh, local ingredients and seafood, but you’ll have more comfort food options like burgers at the tavern. They also have a kid’s menu, so you can make it a family affair.
5. In Fact, Explore All The Amazing Restaurants!
The Brushmill is an excellent choice for a meal in Chester, but there’s such a wonderful culinary presence in this charming little town. One of the reasons it’s worth an overnight stay, or a weekend getaway, is because it’ll be tough to choose where to eat during your visit.
Grano Arso is an award-winning restaurant on Main Street that specializes in handmade pasta dishes. In fact, the chef competed on Beat Bobby Flay! Although he didn’t win the final competition, it was so great to see Chester, CT represented on such a high-profile show.
Otto is another amazing place for something a bit more casual – their wood-fired pizzas are to die for, and were incredibly authentic, and they also make great cocktails. I also suggest getting a table outside on their really nice seasonal patio area that sits along the brook, which is really relaxing. Most tables are shaded, too, which is perfect for hot summer days.
The Villager is an awesome breakfast spot, and you also can’t go wrong with The Village Bistro.
6. Take A Scenic Walk At Cockaponset State Forest
Cockaponset is Connecticut’s largest state forest, and if you’re in Chester for more than a few hours, it’s worth checking out. With over 17,000 acres to explore in the forest, there are some scenic nature trails to enjoy, as well as bike paths, dirt biking trails, and picnic areas.
While there are quite a few trails to explore, for an easy and scenic walk, I recommend doing the loop around the lake, which is really peaceful.
7. Enjoy Concerts In The Garden
On Saturday nights in the spring and summer, the Leif Nilsson Spring Street Studio & Gallery hosts a really lovely Concerts in the Garden series. They invite you to bring a picnic and a bottle of wine, and enjoy a concert out in their amphitheater, which has bistro seating for guests.
The atmosphere is really whimsical and intimate, and each event features new artists and performers. If you happen to be around on a Saturday night, this is definitely something to have on your radar!
8. Ride The Chester-Hadlyme Ferry
Believe it or not, this little ferry is a designated Connecticut landmark! Crossing the Connecticut River seasonally from April through November, the Chester-Hadlyme ferry has been in operation since 1879 (but of course, it’s gone through some updates over the years).
Taking visitors from Chester to the town of Hadlyme, its most notable feature is that it saves you driving time to get to Gillette Castle (which I’ll go more into later in the post). And as you cross the river, it also provides a pretty epic view of the castle.
The ferry is only located a few minutes from Main Street, making it really easy to get there. And whether you just want to hop on as a pedestrian for a quick cruise along the river, or you want to take your car to the other side, it’s a fun and scenic thing to do when in the area. It’s also very affordable.
9. Visit Chakana Sky Alpacas
Chakana Sky Alpacas is such a wonderful fun thing to do while visiting Chester, and what I love about the farm is their respect for the heritage of these beautiful creatures, and the indigenous people who once raised them.
During your visit, Farmer Bill will show you around the small farm, and introduce you to all the adorable alpacas. You’ll get to know all their different personalities, and fun stories about their life on the farm. You may also get the chance to feed and pet them.
There’s also a nice little farm stores to shop from during your visit, and the lovely owners welcome you to bring a picnic and spend time enjoying the atmosphere of the farm. All money made from tours and the farm stores goes into funding their farm, too, so you can feel about your visit.
Pro Tip: Advanced online bookings are now required to visit the farm to streamline the process. Be sure to purchase your admission online before making a special trip.
10. Visit The Fall Back Spring Ahead Craft Fair
Every year in October, the Chester fairgrounds hosts the very cool Fall Back Spring Ahead Craft Fair, where proceeds go toward the community’s EMS and Firefighter organizations. During the fair, you’ll find awesome artisan and craft vendors, and yummy food to purchase! The event is held during the day, and is open rain or shine.
11. Shop The Chester Holiday Market In December
Every Sunday between Thanksgiving and Christmas, one of the best things to do in Chester, CT to get into the holiday spirit is attend the Holiday Market. And since the town is so quaint and idyllic as it is, it’s even more magical during the holidays!
During the market, sidewalks are lined with local food vendors and artisans, making this a wonderful way to shop small, and restaurants are offering up special seasonal menu items to make the day extra special. Honeycone even offers some really delicious seasonal ice cream creations for the event.
Be sure to keep an eye out for Mrs. Claus, as she’s been known to stroll down Main Street during the market, too!
Fun Things To Do Near Chester, CT
Chester is more than worth visiting in its own right, but since it’s a fairly small town, I wanted to showcase a few great things to do nearby in case you wanted to extend your time in this area. Here are all my suggestions on the best things to do near Chester, CT.
12. Explore Gillette Castle State Park
One of the top attractions in all of Connecticut is Gillette Castle State Park, and this is definitely something you’ll want to have on your itinerary when you visit. And as mentioned earlier, a really cool way to get there is by taking the Chester-Hadlyme Ferry. The ferry is also where you’ll get the best landscape view of the castle, so it’s almost worth it just for that.
Gillette Castle is a medieval-style castle built by actor William Gillette, and tours of the inside are available late May through the summer season. However, the grounds are open year-round.
The entire area will make you feel like you’re in Europe, and there are also tons of scenic hiking and walking trails on the grounds, and places to enjoy a picnic.
13. Take In A Show At Goodspeed Opera House
Located in East Haddam, which is less than 10 minutes from Main Street in Chester, the Goodspeed Opera House is a wonderful venue to add to your itinerary if you enjoy live performances.
Build in 1877, the building was originally commissioned by a local banker, and was eventually turned into the venue it is today in the 1960s. Between the amazing talents that grace the stage, and the incredible location right along the scenic river, it’s such a treat to take in a show here.
14. Explore The Cute Town Of Essex
About 10 minutes away from Chester, you’ll find Essex, which is another charming little town that’s perfect for an afternoon or getaway in Connecticut. It’s so cute, in fact, a few Christmas movies have filmed there!
Essex has an amazing Main Street with fun shops and restaurants, a lovely little park, great museums, waterfront dining and so much more. Even though this town is also small, it’s easy to spend at least an afternoon here and not run out of things to do.
15. Spend The Afternoon In Mystic
About 40 minutes east of Chester is the lovely town of Mystic, and if you’re planning a weekend getaway to Chester, it’s worth considering adding on a day trip to this awesome riverfront town. While it was made famous by the movie, it’s continued to maintain its charm throughout the years.
Mystic has an awesome museum that I absolutely love – the Mystic Seaport Museum. It’s also packed with amazing restaurants, scenic riverfront views, great shops, and even a few vineyards nearby in Stonington.
Where To Stay In Chester
There aren’t actually any accommodations right in Chester (which definitely adds to its charm!),
but there are some awesome places to stay nearby.
Here are my recommendations on places to stay near Chester.
The Riverwind B&B is such a wonderful choice for a weekend in Chester. And bonus, it’s also pretty close to Essex! Rooms are decorated in a perfect, historic New England style, and reservations include a full country breakfast with locally-roasted coffee, and lovely outdoor spaces for sharing a bottle of wine.
The Griswold Inn is kind of famous in New England, and has even been featured in some of those Christmas movies I mentioned earlier in the post! For a classic and historic New England inn, it’s hard to beat. It’s also perfectly located on Main Street in Essex village, so you can walk to all the shops and restaurants, and has wonderful dining areas on-site.
Where To Park In Chester, CT
If you happen to visit on a weekend, you may not be able to find street parking close to Main Street. But don’t worry because there’s a very easily solution: park in the Maple Street Public Parking Lot (it will come right up in Google Maps). This lot has an easy walking path that takes you right to the start of Main Street, and isn’t far at all.
If by chance there are no spots in that lot, you can park at the Water Street Public Parking Lot, which will also come up in Google Maps.
How Long Do You Need To Visit Chester?
Chester is a very small town, and you can easily see it in just a couple of hours if you’re short on time. But to experience a restaurant during your visit, have time to stroll the boutiques, and also swing by Little House Brewing, you’ll want a half day, if not more.
Chester also makes for a lovely overnight or weekend getaway, which would allow you to see some of the nearby attractions and towns mentioned. A long weekend getaway to both Chester and Essex would be wonderful!
What Is Chester, CT Known For?
Chester, CT is known for having a distinctly whimsical Main Street with independent shops, as well as an incredible culinary scene. It’s also known as a top day trip destination in Connecticut because it’s very close to famous attractions like the Goodspeed Opera House and Gillette Castle.
More posts you may enjoy:
- Best Things To Do In Mystic, CT
- Best Things To Do In Essex, CT
- Summer In Connecticut: Best Things To Do!
- Summer In New England: Where To Go & What To Do!
That’s A Wrap On The Best Things To Do In Chester, CT
Now that you know all about the best things to do in Chester, CT, hopefully you’re already daydreaming about spending some time here. It really is one of the best places in the state to truly unwind, enjoy a beautiful afternoon, and eat some delicious food. Whether you’re after a peaceful getaway or just a few hours of inspiring relaxation, Chester is likely to be perfect for your next trip.