Pioneer Valley History

Dates represent the time these towns were settled by Europeans. Only the year of settlement is considered, not month or day, so it is possible some towns settled in the same year are actually listed out of order chronologically.
(Dates taken from: https://www.sec.state.ma.us/cis/cisctlist/ctlistalph.htm )

The four Quabbin towns of Dana, Enfield, Prescott, and Greenwich are missing until I can find better data about when they were settled. (Dana was actually Worcester county anyway.)

Agawam - 1635
Springfield - 1636
Longmeadow - 1644
Chicopee - 1652
Northampton - 1654
Hadley - 1659
South Hadley - 1659
West Springfield - 1660
Westfield - 1660
Hatfield - 1661
Easthampton - 1664
Whately - 1672
Deerfield - 1673
Northfield - 1673
Sunderland - 1673
Greenfield - 1686
Amherst - 1703
Brimfield - 1706
Monson - 1715
Ware - 1717
Holland - 1725
Wales- 1726
Granby - 1727
Palmer - 1727
Leverett - 1730
Wilbraham - 1730
Belchertown - 1731
Southampton - 1732
Colrain - 1735
Williamsburg - 1735
Shutesbury -1735
Blandford - 1735
Granville - 1736
New Salem - 1737
Bernardston- 1738
Leyden - 1738
Pelham - 1738
Warwick - 1739
East Longmeadow - 1740
Hampden - 1741
Charlemont - 1742
Ashfield - 1743
Holyoke - 1745
Orange - 1746
Montague - 1750
Tolland -1750
Ludlow - 1751
Wendell- 1754
Shelburne- 1756
Hawley - 1760
Chesterfield - 1760
Chester - 1760
Goshen - 1761
Conway - 1762
Westhampton - 1762
Rowe - 1762
Cummington- 1762
Worthington - 1764
Heath - 1765
Montgomery - 1767
Huntington - 1769
Plainfield - 1770
Southwick - 1770
Gill - 1776
Buckland -1779
Middlefield - 1780
Russell - 1782
Monroe - 1800
Erving - 1801

Nearby Cities:
Albany - 1614*
New York - 1624* 
Boston - 1625
Hartford -1636*
Worcester - 1673 
Brattleboro - 1723*
Pittsfield - 1752

*Dates taken from Wikipedia