Western Mass Events: Fall & Holiday 2026

The Big E, fall festivals, parades, road races and Bright Nights around Springfield, the Pioneer Valley, Franklin County and the Berkshires. We keep this list updated every week.

Updated September 26, 2026. 28 events. Dates come from each organizer’s page; confirm before you go.

Happening now

• Apr 14 – Nov 3: Northampton Tuesday Market — Northampton, Downtown plaza · Free
  Grow Food Northampton's weekly Tuesday farmers market; 2026 season ends November 3.
• May 9 – Oct 10: Pittsfield Farmers Market (outdoor season) — Pittsfield, Pittsfield Common · Free
  Saturday farmers market, 9am-1pm; indoor market continues second Saturdays from November 14.
• Sep 18 – Oct 4: The Big E — West Springfield, Eastern States Exposition
  New England's great state fair with exhibits, food, rides, shows and state buildings.

September 2026

• Sep 26–27: Hancock Shaker Village Country Fair — Pittsfield, Hancock Shaker Village
  Annual country fair with antique car show, crafts and farm activities.
• Sep 26–27: North Quabbin Garlic & Arts Festival — Orange, Forster Farm
  28th annual festival of garlic food, arts and crafts and music.

October 2026

• Sun, Oct 4: Festival of the Hills — Conway, Conway town center
  Hilltown festival with music, crafts, road race and parade.
• Sun, Oct 4: North Adams Fall Foliage Parade — North Adams, Route 8 to Main St · Free
  70th annual fall parade through downtown, 1-3pm.
• Oct 10–11: Ashfield Fall Festival — Ashfield, Main Street
  Crafts, art, local food, music and dance on Ashfield's Main Street, 10am-5pm.
• Oct 10–11: Berkshire Botanical Garden Harvest Festival — Stockbridge, Berkshire Botanical Garden
  Fall harvest festival, 10am-5pm; $15 adults, kids under 12 free.
• Mon, Oct 12: Greylock Ramble — Adams, Adams Visitor Center · Free
  Annual Columbus Day hike up Mount Greylock, preceded by RambleFest on Oct 11.
• Sat, Oct 17: Doors Open Holyoke — Holyoke, Multiple locations citywide · Free
  Citywide open-house day at historic and notable Holyoke buildings.
• Sat, Oct 17: Westfield PumpkinFest — Westfield, Amelia Park athletic fields · Free
  10th annual free fall festival with pumpkin carving, music and games, 11am-3pm.
• Fri, Oct 30: Pittsfield Halloween Parade — Pittsfield, Tyler Street · Free
  80th annual Halloween parade, 7pm, theme "Futuristic Frights."

November 2026

• Sun, Nov 1: Western Mass 10 & NoHo 5K — Amherst to Northampton, UMass Amherst to Union Station
  Point-to-point 10-miler along the Norwottuck Trail plus a Northampton 5K.
• Nov 6–8: Franklin County CiderDays — Franklin County (multiple towns), Orchards and venues countywide
  Weekend of cider tastings, orchard tours and demonstrations across Franklin County.
• Nov 7–8: Crafts of Colrain Studio Tour — Colrain, Artisan studios townwide · Free
  Self-guided open-studio tour of Colrain artisans, 10am-4pm.
• Sun, Nov 8: U.S. Army Field Band Concert — Springfield, Symphony Hall
  Spirit of Springfield concert by the U.S. Army Field Band, 2pm.
• Wed, Nov 11: North Adams Veterans Day Parade — North Adams, Main Street · Free
  Veterans Day parade downtown, 10:30am.
• Wed, Nov 11: Springfield Veterans Day Parade — Springfield, Steps off at STCC · Free
  City Veterans Day parade stepping off from Springfield Technical Community College at 11am.
• Sat, Nov 21 (ongoing): NightWood at The Mount — Lenox, The Mount
  Ticketed outdoor sound-and-light show in The Mount's woodlands; closing date not yet posted.
• Tue, Nov 24: North Adams Tree Lighting — North Adams, Monument Square · Free
  City holiday tree lighting, 5:30-7pm.
• Nov 25 – Jan 3, 2027: Bright Nights at Forest Park — Springfield, Forest Park
  Drive-through holiday light display; closed Nov 30 and Dec 1.
• Mon, Nov 30: Bright Nights 5K Road Race — Springfield, Forest Park
  Evening 5K through the Bright Nights displays, 6:30pm.

December 2026

• Dec 4–12: Yuletide at Storrowton — West Springfield, Storrowton Village Museum
  Holiday program with free first-weekend activities, then paid tours and lantern-light events.
• Dec 5–6: Stockbridge Main Street at Christmas — Stockbridge, Main Street
  37th annual recreation of Norman Rockwell's holiday Main Street scene.
• Sun, Dec 6: Hot Chocolate Run for Safe Passage — Northampton, Hampton Ave & Old South St
  Annual charity run/walk benefiting Safe Passage.
• Sun, Dec 13: Spirit of Springfield Holiday Concert — Springfield, Symphony Hall
  Annual Spirit of Springfield holiday concert, 2pm.
• Thu, Dec 31: North Adams New Year's Eve Ball Drop — North Adams, Center Street parking lot · Free
  Family New Year's Eve ball drop, 8-9pm.