Home Food + DrinkBars How to Spend the Day in Chester, New Jersey

How to Spend the Day in Chester, New Jersey

by Jean Lee
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While driving down Main Street in Chester, New Jersey, visitors and locals alike may briefly forget they are in New Jersey, but perhaps in a movie set depicting an idyllic small town. Being just under an hour by car from the Hoboken area, this small New Jersey town has no shortage of fun activities and great food spots to try. Depending on the time of year, there is always something fun to do in Chester, including flowers, farms, and fresh food. Keep reading for a complete rundown on how to spend a delightful day in Chester, New Jersey.

black river candy shop chester

^ Black River Candy Shop

The History

Incorporated in 1799, Chester was a central point for trading goods in the area, and it was known over the years for its farming, mining, and manufacturing. The town has some interesting ties to the Jersey City area, including how stagecoaches would travel to the town from Paulus Hook as a common route. Also, iron was sent from the mines to manufacturing facilities in Jersey City via the Morris Canal.

Traveling Here

These days traveling is much easier than during the 19th Century, and visitors can travel via car, trains, or buses. Travelers can hop on Route 78 and be to the center of Chester in just under an hour (without traffic). Without a dedicated train and bus station, travelers can take mass transportation to one of the nearby stops including Peapack-Gladstone, Morristown, or Dover, and then catch an Uber from there.

Where to Eat

Maria’s | 56 Main Street

Start the day at Maria’s to get a coffee or specialty drink. The menu includes specialty lattes, iced teas, paninis, and baked goods. Sitting outside makes for some lovely people watching, but seating overall is limited.

Chester Bagel | 17 Main Street

Locals love this classic breakfast and lunch spot, and the line can sometimes be out the door. While the breakfast bagel sandwiches are a favorite, don’t sleep on the cold cut sandwiches which are named after famous places and celebrities.

Marilyn’s Cafe | 21 W Main Street

New Jersey is known for its diners, and this cafe is no exception. The walls are plastered with photos of Marilyn Monroe and other paraphernalia, making patrons feel like they are stepping back in time. Everything is good, but diners can’t go wrong with one of the omelets. 

Read More: A Weekend Getaway to Murrells Inlet, South Carolina

The Old Mill Tavern | 55 Route 24

old mill tavern Chester

This local watering hole has burgers, wings, 24 beers on tap, and much more. Eat indoors or out at this classic bar just outside of downtown. The location makes it a perfect pit stop before or after a nice hike, as Hacklebarney State Park and other trails aren’t far away. More than 100 patches of police, fire, and other first responders are on the wall, and all veterans, police, fire, and emergency members receive a 10% discount every day. 

Aztec Mexican Restaurant | 35 Perry Street

aztec mexican restaurant chester

Located just off of Main Street, Aztec Mexican Restaurant has authentic and delicious Mexican fare for visitors to enjoy. Customers can try various tacos, burritos, enchiladas, and more. However, we keep coming back for the chimichanga (try the chicken tinga). 

Taylor’s Ice Cream Parlor | 18 Main Street

tayors ice cream Chester

This small-town ice cream shop has big flavor. A favorite for the kiddos after a tough summer baseball or softball game, Taylor’s Ice Cream Parlor has all of the delicious toppings and tons of flavors like classic rocky road and mint chocolate chip, to cotton candy, YooHoo, and more. 

Chester Meat Market | 27 W Main Street

chester meat market

While it may not have ready-to-eat meal options, this shop has plenty of meat and other choices like raviolis and spice rubs to make a fantastic dinner to end a great day in Chester. While there isn’t a bad choice of meat, if hamburgers are a favorite, make sure to get a pack because locals absolutely love them.

Things To Do

Hiking and Parks

There are many trails to try in the area, each with its special characteristics. Some options include Patriots Path, a 90-mile trail running through New Jersey with several access points in Chester, trails around the Cooper Grist Mill, Hacklebarney State Park, and more. 

hiking chester

^ Black River Park

Visitors bringing kiddos can also head to a few great parks with fun play areas including Chubb Park and Grove Street Park. 


There seems to be no shortage of farms in the Chester area, and a few may even look familiar as they are staples for farmer’s markets in the Jersey City area. Alstede Farms and Stony Hill Farms are both Chester favorites, and have seasonal produce and goods, as well as corn mazes in the Fall months. 

Alstede farms chester

^ Alstede Farms

Riamede Farm and Hacklebarney Farm Cider Mill is another favorite with sprawling apple orchards.

See More: A Weekend Trip Guide to Philadelphia, PA

Seasonal Activities

Speaking of fall months, Chester is known for its seasonal activities, especially its corn mazes in the fall. Twice a year, Chester has craft shows when artists and small businesses line the grassy field off of Main Street. The next weekend fair will be June 4-5, 2022, and admission costs $4. 

During the summer, there is a food truck festival where local food trucks congregate in the same field, and live music is performed in the town’s gazebo. The dates for 2022 will be announced soon.  

^ Where the Festival of Trees is held

The cold winter months don’t stop this town from continuing to host fun activities including a yearly Christmas Tree Lighting or Festival of Trees which lights showcases decorated trees for purchase (check the Chester Township page for more information).

Shopping on Main Street

Perhaps one of the most charming streets in town, Main Street is a must-see stop on any visit to see the cute stores and delicious food options. Antique shoppers can check out Chester Crafts, Collectibles + Antiques (28 Main Street), along with other specialty gift shops including Perfect Treasure (47 Main Street), Fizzle Creations (87 Main Street), and the Dainty Dandelion (58 Main Street). 

perfect treasure chester

^ Perfect Treasure Gift Shop

The Olive and the Stone (58 Main Street) is a fun stop to try out various olive oil and vinegar pairings.

Another delicacy is The Maple Shop (105 Main Street) which sells 100% Vermont Maple Syrup among other yummy treats. 

No trip to Chester is complete without a visit to the Black River Candy Shoppe (44 Main Street) to get some candy by the piece or in bulk.

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