The Town Files

The 25 Hippest Small Towns in New York

Ranked on The Town Files lifestyle rankings among 707 towns of 2,500–10,000 people in New York. #1 is Nyack, NY.

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Numbers match the ranking.
The 25 Hippest Small Towns in New York1. Nyack100th pct2. Tuckahoe100th pct3. East Rochester100th pct4. Hudson100th pct5. Saugerties100th pct6. Piermont100th pct7. Great Neck Plaza99th pct8. Norwich99th pct9. Woodstock99th pct10. Mechanicville99th pct11. Ballston Spa99th pct12. Hamilton99th pct13. New York Mills99th pct14. Shandaken99th pct15. Rhinebeck99th pct16. Greenport99th pct17. Lewiston99th pct18. Woodstock99th pct19. New Paltz98th pct20. Brockport98th pct21. Menands98th pct22. Owego98th pct23. Whitesboro98th pct24. Hudson Falls97th pct25. Scotia97th pct
  1. 25Scotia, New York

    Hipper than 97% of New York towns

    7,272 people · Schenectady County · median home $189,900 · income $76,525 · Jan low 16°F · 59 in snow

  2. 24Hudson Falls, New York

    Hipper than 97% of New York towns

    7,427 people · Washington County · median home $165,200 · income $62,969 · Jan low 10°F · 62 in snow

  3. 23Whitesboro, New York

    Hipper than 98% of New York towns

    3,612 people · Oneida County · median home $160,700 · income $45,934 · Jan low 14°F · 164 in snow

  4. 22Owego, New York

    Hipper than 98% of New York towns

    3,654 people · Tioga County · median home $147,300 · income $60,139 · Jan low 16°F · 49 in snow

  5. 21Menands, New York

    Hipper than 98% of New York towns

    4,554 people · Albany County · median home $271,300 · income $80,583 · Jan low 17°F · 56 in snow

  6. 20Brockport, New York

    Hipper than 98% of New York towns

    7,104 people · Monroe County · median home $157,700 · income $69,866 · Jan low 18°F · 77 in snow

  7. 19New Paltz, New York

    Hipper than 98% of New York towns

    7,324 people · Ulster County · median home $414,500 · income $52,774 · Jan low 19°F · 59 in snow

  8. 18Woodstock, New York

    Hipper than 99% of New York towns

    2,521 people · Ulster County · median home $675,600 · income $52,091 · Jan low 12°F · 86 in snow

  9. 17Lewiston, New York

    Hipper than 99% of New York towns

    2,531 people · Niagara County · median home $238,100 · income $73,821 · Jan low 19°F · 55 in snow

  10. 16Greenport, New York

    Hipper than 99% of New York towns

    2,583 people · Suffolk County · median home $961,200 · income $81,094 · Jan low 23°F · 26 in snow

  11. 15Rhinebeck, New York

    Hipper than 99% of New York towns

    2,697 people · Dutchess County · median home $492,600 · income $70,496 · Jan low 11°F · 61 in snow

  12. 14Shandaken, New York

    Hipper than 99% of New York towns

    2,866 people · Ulster County · median home $346,100 · income $66,031 · Jan low 12°F · 105 in snow

  13. 13New York Mills, New York

    Hipper than 99% of New York towns

    3,244 people · Oneida County · median home $207,700 · income $57,578 · Jan low 14°F · 164 in snow

  14. 12Hamilton, New York

    Hipper than 99% of New York towns

    4,107 people · Madison County · median home $264,200 · income $66,750 · Jan low 11°F · 77 in snow

  15. 11Ballston Spa, New York

    Hipper than 99% of New York towns

    5,111 people · Saratoga County · median home $308,200 · income $101,667 · Jan low 14°F · 64 in snow

  16. 10Mechanicville, New York

    Hipper than 99% of New York towns

    5,163 people · Saratoga County · median home $186,500 · income $50,675 · Jan low 17°F · 60 in snow

  17. 9Woodstock, New York

    Hipper than 99% of New York towns

    6,287 people · Ulster County · median home $604,700 · income $92,118 · Jan low 12°F · 86 in snow

  18. 8Norwich, New York

    Hipper than 99% of New York towns

    7,051 people · Chenango County · median home $121,100 · income $53,333 · Jan low 12°F · 75 in snow

  19. 7Great Neck Plaza, New York

    Hipper than 99% of New York towns

    7,482 people · Nassau County · median home $416,100 · income $92,474 · Jan low 27°F · 19 in snow

  20. 6Piermont, New York

    Hipper than 100% of New York towns

    2,517 people · Rockland County · median home $652,900 · income $140,450 · Jan low 23°F · 33 in snow

  21. 5Saugerties, New York

    Hipper than 100% of New York towns

    3,899 people · Ulster County · median home $374,100 · income $57,778 · Jan low 12°F · 86 in snow

  22. 4Hudson, New York

    Hipper than 100% of New York towns

    5,894 people · Columbia County · median home $389,900 · income $54,139 · Jan low 18°F · 31 in snow

  23. 3East Rochester, New York

    Hipper than 100% of New York towns

    6,334 people · Monroe County · median home $143,500 · income $73,344 · Jan low 19°F · 91 in snow

  24. 2Tuckahoe, New York

    Hipper than 100% of New York towns

    7,084 people · Westchester County · median home $621,300 · income $104,375 · Jan low 23°F · 33 in snow

  25. 1Nyack, New York

    Hipper than 100% of New York towns

    7,265 people · Rockland County · median home $628,200 · income $116,649 · Jan low 23°F · 33 in snow

Price vs ranking

Median home value vs ranking, New York towns0255075100$81K$426K$771K$1116K$1462KMedian home valuePercentile
Orange squares are the 25 towns on this list; green dots are other towns on The Town Files in New York.

More New York rankings

Same ranking, other places

Methodology. We ranked 707 towns of 2,500–10,000 people in New York (2020 Census population; towns with 2,500+ people have pages so far). Lifestyle measures are The Town Files lifestyle rankings, built from federal demographic, school, crime and housing data (2025), shown as percentiles. Only towns better than 60% of their peers on this measure qualify, so lists can be shorter than 25. Sources: