Wenham, #1 on this list · Photo: Fletcher6 · CC BY-SA 3.0
Massachusetts rankings · 2026
Best small towns in Massachusetts
Wenham ranks first of Massachusetts’ 98 graded small towns (2,500–9,999 residents), with an A+: jobs & income (A+) and hazard risk (A+) are its strongest grades; walkability (B+) is its lowest. 40 of the 98 (41%) grade A− or better nationally, against 25% of U.S. towns.
The overall grade, sorted: cost of living, safety, schools, health, jobs & income, walkability and hazard risk, from Census, FBI, state, CDC, EPA and FEMA data. How grades work
Where they are: Four of the top 10 are in Essex County.
All 98 small towns
Overall score, highest first. The score (0–100) blends the seven livability grades and sets the order; the letter places that score among every U.S. town of 2,500+, and A+ is the top 5%, so neighbors on the list often share a letter. Each town links to its page, where the grade sheet shows every subject. The rank is the town’s place among all 282 Massachusetts towns.
224Great BarringtonBerkshire County · 7,239 people48.2bottom 38.6%C+Strongest: walkability A+, health A−·lowest: cost of living D−
228HardwickWorcester County · 2,736 people48.0bottom 38.0%C+Strongest: safety B+, hazard risk B·lowest: schools C
230BarreWorcester County · 5,641 people47.8bottom 37.2%C+Strongest: jobs & income B+, hazard risk B·lowest: schools C
237LeeBerkshire County · 5,673 people45.6bottom 31.8%CStrongest: walkability A, health A−·lowest: cost of living D
238WarrenWorcester County · 5,122 people45.4bottom 31.2%CStrongest: safety B, hazard risk B·lowest: walkability D
248SheffieldBerkshire County · 3,314 people41.7bottom 22.7%C−Strongest: health A−, walkability B·lowest: cost of living D−
251ProvincetownBarnstable County · 3,729 people40.9bottom 20.9%C−Strongest: walkability A+, health A−·lowest: schools D
253North BrookfieldWorcester County · 4,793 people40.4bottom 19.6%C−Strongest: hazard risk B, health B·lowest: schools C−
254MonsonHampden County · 8,175 people39.3bottom 17.7%C−Strongest: jobs & income B, hazard risk B−·lowest: schools C−
258MontagueFranklin County · 8,377 people37.4bottom 14.2%DStrongest: walkability A−, health B+·lowest: schools D
270AdamsBerkshire County · 7,934 people32.4bottom 7.3%DStrongest: walkability B−, health B−·lowest: hazard risk D
273OrangeFranklin County · 7,569 people30.3bottom 5.2%DStrongest: walkability B+, safety B−·lowest: schools D
Method
How this list is made
Each town’s overall grade blends seven livability grades: cost of living (weight 18), safety (18), schools (16), health (14), jobs & income (12), walkability (8) and hazard risk (4). A town needs 2,500+ residents and three of the first four. Letters are national, so an A here means the same as an A in any state; the list is the same towns in the same order, ranked within Massachusetts. Towns without their own FBI figures are graded on the rest and their page says why.
Data years: crime 2023–2025 (FBI), Census ACS 2020–2024, CDC PLACES 2025, state school tests. How grades work
Quick answers
Questions people ask
What is the best small town in Massachusetts?
Among 98 graded towns of 2,500 to 9,999 residents, Wenham (Essex County) ranks first, with an A+; jobs & income (A+) and hazard risk (A+) are its strongest grades; walkability (B+) is its lowest. Carlisle and Boxford follow.
How are these towns ranked?
By the overall grade, which blends seven livability grades from public data. The letter is national; the rank is within Massachusetts. The full method is on How grades work.
Why isn’t my town on this list?
The list covers towns of 2,500 to 9,999 residents with an overall grade (98 in Massachusetts). 42 smaller places have subject grades only; Larger towns are on the best places to live list. Every town is on the Massachusetts page.
Go deeper
More Massachusetts lists
Every list ranks the same 2,500+ towns, so a town’s rank means the same thing on each.