Chester, Vermont: Helping Hands & Wine, Cheese, Pies, Candy, Donuts, and More

Have you ever visited the small town of Chester, Vermont? 

While in Vermont, I visited my good friend, Christopher Meyer, who founded, with Jason Tostrup of the Free Range restaurant, a charitable, non-profit organization called Chester Helping Hands. It was established during the pandemic to provide food assistance for the local community, such a worthy cause. They currently offer free meals on Wednesdays, provided by local restaurants. They are also supporting local farmers who have provided foods for this program as well. All of these meals are financed through donations, and the workers who help disseminate the meals are volunteers.

On the Wednesday I was in Vermont, Chris and Chester Helping Hands set up their table on The Common in Chester, a street with a number of small businesses, from an antiques shop to a book store. A line of cars queued up to receive their free mails, and about 700 meals were ultimately disseminated. The process ran smoothly and it was inspiring to see how this community has come together to help each other during these tough times. Not only do local residents receive free food, but restaurants and farms receive support as well, helping them as they too are hurting because of the pandemic. 

If you would like to support Chester Helping Hands, you can Venmo them a donation to @ChesterHelpingHands. As they are a 501c3 organization; your donations should be tax-deductible. I'm proud of my friend Chris for having developed such an admirable program.

In the vicinity of The Common in Chester, there's a number of cool food and drink shops too. I made brief stops to a few of these places, although I would like to explore them in more depth in a future trip. Chester is a small town, of only about 3,000 people, but its worth your while to explore this interesting community. Here's a few spots I'd highly recommend you check out.

The Meditrina Wine & Cheese shop is an excellent place with a very compelling beer and wine selection, and some gourmet foods. It's a small store, but there's plenty of food and drink available, filling the shelves floor to ceiling, and I bet you find plenty to tantalize you. The shop also conducts regular wine tastings. I spoke briefly with Amy Anderson, the owner of the shop, and she evidenced the passion for wine I seek from such shop owners. I probably could have sat down with her and spoke about wine for hours.

There is a section of Vermont cheese and gourmet foods, including Torres Potato Chips, one of my favorites. If you're going to drink wine or beer, it's always pleasant to have some snacks too.

There's also a section of local beers and ciders, and this is where I bought the Shacksbury Whistlepig Lo-Ball. Vermont is well known for its craft beers, and there certainly was a wide variety of local offerings for sale. 

These photos are just a small section of the wine shop, and as I skimmed the wine shelves, I found much that appealed to me, including plenty of natural wines, small production wines, and some other intriguing wines, including a Red Vinho Verde (which I bought). They have wine at all price points and any wine lover will find much of interest. This well-curated selection would be impressive wherever it was located. Finding it in the small town of Chester was intriguing and all wine lovers need to make this a stop while they are in southern Vermont.

These "bears" stand outside the Chester Candy Company, a small spot that concentrates primarily on sweet treats made in Vermont and New England. There's plenty of decadent chocolates, fudge, retro-candies, gummies, sours, hard candies, and much more. I enjoyed their Dark Chocolate Bourbon Caramels, which certainly had a prominent bourbon taste. 

Another cool spot is the Southern Pie Company (of which I sadly didn't get any pics), which specializes in pie, especially with a southern flair. Bourbon Pecan Pie, Chess Pie, Buttermilk Pie, Sur Cream Peach Pie, and so much more. The pies looked awesome, and I was very tempted to pick up a pecan pie, but I already had too many treats at the moment. However, they also make some other baked goods, and I got some of their tasty, fudgy brownies. I will get some pie on my next visit. In addition, you'll find a variety of breakfast and lunch sandwiches, and have a variety of drinks, including various coffees. 

Less than a mile away, you should visit Smitty's Chester Market, a small grocery store with plenty of the usual items, as well as a meat counter, beer & wine, and a deli. I visited the deli a couple times, which sells a variety of customizable sandwiches, as well as salads, soups, mac n' cheese, and other dishes. Every day, there is something different offered on the menu.

Their sandwiches are ample, fresh, tasty, and reasonably pricesd. They are also made for take-out only as they don't have a dining area. In addition, they sell a variety of baked goods, made in-house, including amazing Apple Cider Donuts, dipped in cinnamon/sugar, and a hearty Cinnamon Bread. Get there early as those baked goods disappear quickly. 

And you can ever buy worms and nightcrawlers at Smitty's if you want to do some fishing in Vermont lakes and rivers.

So, when will you take your next trip to southern Vermont?