Places in Chester
Farms, markets & local spots in Chester
73 places in Chester: 10 places to eat and drink, 2 shops, 22 things to do and 2 places to stay. Local spots first, with directions to every one.
All places
73
59 per 1,000 residents
Eat & drink
10
8.1 per 1,000 residents
Shops
2
Things to do
22
19 outdoors · 1 landmarks
Places to stay
2
1.6 per 1,000 residents
What kind of places does Chester have?
Read from every listing. The page puts what stands out first.
The map
Where Chester gathers
31 of Chester’s 73 places sit within a five-minute walk of Middlefield Rd.
31places in a five-minute walk of Middlefield Rd42% of Chester’s places
★ What stands out · Eat & drink
See all →10 places to eat & drink
5 farms & markets, 4 restaurants, 1 bars & breweries. Local spots first.
Shops
See all →2 shops
1 clothing, 1 more shops. Local spots first.
Things to do
See all →22 things to do
19 parks & outdoors, 2 fitness & sports, 1 history & landmarks. Local spots first.
Everyday
See all →21 errands & services
Groceries, gas, the barber, the vet, the bank.
Offices & pros 4United States Postal Service · Slnlaw Hilltown Law Office · Wheeler Oil CoHome services 2Bolduc Mechanical Services · Jeff's Oil Burner ServiceBanks & insurance 2Kam Financial Group · Chester Town Tax CollectorGroceries & convenience 1Chester Village MarketAuto & gas 1Legacy Motor CarsHair & beauty 1Chester Village CutsOther services 10Littleville Fair · marc civitarese · AA Welding
Community
See all →16 schools, churches & public places
Where Chester learns, worships and gets things done.
Town & public services 7Town of Chester · Chester Fire Department · Chester Police DepartmentSchools & childcare 3Chester Elementary School · Chester High School · Country Cuddlers Family DaycarePlaces of worship 3Cornerstone Christian Church · Chester Baptist Church · First Congregational Church of ChesterCommunity groups 3Southern Hilltowns Adult Education Center · Chester Mass History Museum · The Berkshire Flyers
Next door
Chester and its neighbors
Tap a town to see its places.
Places per 1,000 residents · all places listed
Worthington62Chester59Middlefield57Becket49Blandford46Huntington40Talk & tips
Favorites, openings and closings from Chester neighbors.
Weigh in
Is Carm's Restaurant and Coffee Shop the best place to eat in Chester?
Your answer becomes a post in Town Square.
What’s missing?
Not on the map yet. It may just be missing.
No bakery listed ·
No coffee shop listed ·
No hardware store listed ·
Share a tip
Some place details from Overture Maps (CDLA-Permissive-2.0), checked against the Census town line. Places added by neighbors go live once a second neighbor confirms them. Spot a mistake? Open the place and tap Edit mode.
How we sort and count
Each list puts neighbor favorites first (ratings and photos), then the most complete listings (a website, a phone number, a note), with local, independent spots ahead of national chains. Categories come from each place’s map category, so a café filed under “Shops” still shows up with the cafés. “A five-minute walk” is a quarter mile from the busiest spot on the map. Per-1,000 figures use the Census population.