Things To Do

Mohegan Sun Casino

Need we say more?

Main St & Essex Steam Train

Take the family on a two and a half hour narrated journey through the scenic Connecticut River Valley—named one of the “last great places on Earth” by the Nature Conservancy—aboard the only steam train and riverboat connection in the U.S.!

Hammonasset Beach

Watch Hill

Watch Hill is an awesome place to spend a day soaking up some sun and a nice way to check out some of Rhode Island's prettiest areas. This is an ideal summer hangout spot.

Gillette Castle State Park

A real life castle in little ol East Hadaam, truly a sight to behold. Get there by road or hop on the Chester-Hadlyme ferry across the Connecticut River.

Goodspeed Opera House

Perched right on the Connecticut River, this well known theater is host to musicals all year.

Rt 1 & Florence Griswold Museum

Exquisite art, beautiful gardens, gorgeous architecture. OK!

Yale University Art Gallery

Yale (maybe you've heard of it?) has strummed up quite the selection. Well worth the visit!

Chatfield Hollow Brook

Beautiful and relatively easy hikes. Most likely place to spot Jim McDougal.

Dinosaur State Park

Connecticut is home to some of the largest dinosaur track sites in the US. Especially fun for kids!

Mystic Aquarium

Yale Collection of Musical Instruments

I like everything but country and rap.

Ashley's Ice Cream

Ashley's ice cream makes you grow up big and strong. (Try their sweet cream flavor!)

Louis' Lunch

Birthplace of the hamburger

The Place Restaurant

You're sitting on a stump, eating lobster and corn grilled up before your very eyes, and the ground is covered in oyster and clam shells. You're at The Place! Legend has it that every now and then, Will Ferrell can be spotted dining here.

Cristy's Madison

The food here is so good and the servings are huge and it's Jim's favorite restaurant in the area and I'm being forced to include it. Check it out! Especially amazing breakfast options - you should probably get an eggs Benedict and hash. But get anything and it's going to be fantastic. Afterward, walk down to the beach at the Madison Beach Hotel and you've got yourself a nice little morning there.

Jack Rabbit's Burgers, Wings and Things

Thimble Islands

Who's got a boat?

Little House Brewing Company

The most recent addition to Chester's downtown. Super cute, super quaint. It's lovely.

Stony Creek Brewery

Great beer, great spot.

Jonathan Edwards Winery

This winery is gorgeous and has a ton of that New England charm.

Saltwater Farm Vineyard

Winery constructed out of an old airplane hanger. Beautiful spot!

Chamard Vineyards

Another beautiful vineyard! Try their "70/30"

Mystic

Beautiful little village. Stop by for a slice at Mystic Pizza (yeah, that one)