Looking for fall events in MetroWest Boston? September and October bring some of the region’s most popular community festivals, harvest fairs, parades, food truck events, arts celebrations, and family-friendly activities.
From Northborough Applefest and Marlborough’s Labor Day celebrations to historic events in Sudbury and local festivals throughout the region, here are some of the best fall events happening in MetroWest Boston in 2026.
2026 MetroWest Boston Fall Events at a Glance
September 6: Marlborough Labor Day Festival
September 7: Marlborough Labor Day Parade and Milford Labor Day Parade
September 12: Hopkinton Polyarts Festival and Medway Farm Festival
September 13: Marlborough Food Truck & Arts Festival
September 19: Celebrate Holliston, Celebrate Hudson Festival, and Westborough PorchFest
September 20: Holliston Harvest Fair
September 24–27: Northborough Applefest
September 26: Franklin Harvest Festival and Sudbury Colonial Faire & Muster of Fife and Drum
October 3: Ashland Dragonfly Street Faire and Sudbury Apple Fest
October 12: Southborough Heritage Day
Ashland
Dragonfly Street Faire
When: Saturday, October 3, 2026, from 1–6 p.m.
Where: The Corner Spot, 6 Cherry Street, Ashland
Celebrate fall in downtown Ashland at the Dragonfly Street Faire, featuring live music, performers, food, beverages, and community fun at The Corner Spot.
Franklin
24th Annual Harvest Festival
When: Saturday, September 26, 2026, from noon–5 p.m.
Where: Downtown Franklin, Main Street and surrounding areas
The Franklin Harvest Festival brings fall fun to downtown Franklin with more than 150 vendors, live music, activities, artwork, food, crafts, and entertainment.
Visitors can stroll through downtown while supporting local businesses, artists, makers, and community organizations.
Holliston
Celebrate Holliston
When: Saturday, September 19, 2026
Parade: 9 a.m.
Field Day: 10 a.m.–3 p.m.
Where: Damigella Field, Holliston
Celebrate the Holliston community with a morning parade followed by a full day of activities at Damigella Field.
44th Annual Harvest Fair
When: Sunday, September 20, 2026, from 10 a.m.–4 p.m.
Where: Holliston Historical Society, 547 Washington Street
Step into fall at the Holliston Historical Society Harvest Fair, where visitors can browse antiques, crafts, food, and other seasonal offerings in a historic New England setting.
Hopkinton
Hopkinton Polyarts Festival
When: Saturday, September 12, 2026, from 10 a.m.–4 p.m.
Where: Hopkinton Town Common
The Hopkinton Polyarts Festival brings together approximately 75 artists and craftspeople from across New England for a day dedicated to art, handmade goods, and creativity.
It’s a great fall event for visitors looking to shop locally made art and crafts while enjoying the atmosphere of Hopkinton Town Common.
Hudson
Celebrate Hudson Festival
When: Saturday, September 19, 2026, from 1–7 p.m.
Where: Main Street, Hudson
Celebrate the people, businesses, art, food, and culture that make Hudson unique at the Celebrate Hudson Festival.
The downtown event features local music, food, small businesses, art, and community activities along Main Street.
Marlborough
Marlborough Labor Day Festival
When: Sunday, September 6, 2026, from noon–5 p.m.
Where: Main Street and Gold Star Plaza, Marlborough
Kick off Labor Day weekend at the Marlborough Labor Day Festival, featuring live music, local vendors, food trucks, bounce houses, a Touch-a-Truck exhibit, and family-friendly entertainment in downtown Marlborough.
Marlborough Labor Day Parade
When: Monday, September 7, 2026, at noon
Where: Downtown Marlborough
Starting point: Pleasant Street and Lincoln Street intersection
Continue the celebration with the Marlborough Labor Day Parade, one of the city’s signature annual traditions. Expect marching bands, floats, performers, community groups, and plenty of hometown spirit.
Marlborough Food Truck & Arts Festival
When: Sunday, September 13, 2026, from 11 a.m.–5 p.m.
Where: Downtown Marlborough
Spend the day exploring the Marlborough Food Truck & Arts Festival, featuring local artists and makers, food trucks, live performances, a Touch-a-Truck experience, local restaurants, interactive art displays, and more.
Medway
Medway Farm Festival
When: Saturday, September 12, 2026, from noon–4 p.m.
Where: Medway Community Farm, 50 Winthrop Street
Celebrate the season at the Medway Farm Festival, a family-friendly fall event featuring food trucks, a beer tent, live music, vendors, and children’s activities.
Milford
Milford Labor Day Parade
When: Monday, September 7, 2026, at 1 p.m.
Where: Milford High School
Celebrate Labor Day in Milford with the annual Milford Labor Day Parade, beginning at Milford High School and bringing the community together for one of the town’s longtime holiday traditions.
Northborough
Northborough Applefest
When: Thursday, September 24–Sunday, September 27, 2026
Where: Northborough
One of MetroWest Boston’s signature fall celebrations, Northborough Applefest fills several days with community events and seasonal fun.
Visitors can enjoy fireworks, concerts, food trucks, a parade, family activities, and other events throughout Northborough.
Southborough
Southborough Heritage Day
When: Monday, October 12, 2026, from 9:30 a.m.–2 p.m.
Where: Southborough
Celebrate local history and community at Southborough Heritage Day. The annual fall celebration includes a parade, crafts, food trucks, and activities for visitors of all ages.
Sudbury
Apple Fest at the Wayside Inn
When: Saturday, October 3, 2026, from 10 a.m.–2 p.m.
Where: Longfellow’s Wayside Inn, Sudbury
Enjoy a classic New England autumn day at Apple Fest at Longfellow’s Wayside Inn. The event features music, food, a craft market, activities, and seasonal fun on the historic Wayside Inn property.
Colonial Faire & Muster of Fife and Drum
When: Saturday, September 26, 2026, beginning at 10 a.m.
Where: Longfellow’s Wayside Inn, Sudbury
Step back in time at the Colonial Faire and Muster of Fife and Drum in Sudbury.
Visitors can experience a colonial encampment, militia demonstrations, traditional crafts, fife and drum music, a parade, and other activities inspired by early New England history.
Westborough
Westborough PorchFest
When: Saturday, September 19, 2026, from 1–4 p.m.
Where: Westborough
Enjoy an afternoon of live music around Westborough during PorchFest, a community music event that brings performers and neighbors together for an easygoing fall afternoon.
Plan Your Fall Weekend in MetroWest Boston
With festivals, farm events, parades, arts and crafts, live music, food trucks, historic celebrations, and community traditions, there are plenty of reasons to visit MetroWest Boston this fall.
Whether you’re planning a family day trip, a fall weekend with friends, or a seasonal getaway near Boston, September and October offer events throughout Ashland, Franklin, Holliston, Hopkinton, Hudson, Marlborough, Medway, Milford, Northborough, Southborough, Sudbury, Westborough, and beyond.
Be sure to check individual event websites before visiting for the latest schedules, parking information, weather updates, and event changes.
Frequently Asked Questions About Fall Events in MetroWest Boston
What fall festivals are happening in MetroWest Boston in 2026?
MetroWest Boston’s 2026 fall calendar includes Northborough Applefest, the Franklin Harvest Festival, Marlborough’s Labor Day Festival and Food Truck & Arts Festival, Medway Farm Festival, Celebrate Hudson, Southborough Heritage Day, Apple Fest at the Wayside Inn, and several other community events.
What are some family-friendly fall events near Boston?
Family-friendly fall events in MetroWest Boston include Northborough Applefest, Celebrate Holliston, Marlborough’s Labor Day Festival, Medway Farm Festival, Southborough Heritage Day, the Dragonfly Street Faire, and Apple Fest at Longfellow’s Wayside Inn.
Are there fall events in MetroWest Boston with food trucks and live music?
Yes. Several MetroWest fall events feature food trucks, live music, vendors, and entertainment, including Marlborough’s Labor Day Festival, Marlborough Food Truck & Arts Festival, Franklin Harvest Festival, Medway Farm Festival, Celebrate Hudson, and Northborough Applefest.
What fall events in MetroWest Boston feature arts and crafts?
Visitors looking for art and handmade goods can explore the Hopkinton Polyarts Festival, Franklin Harvest Festival, Holliston Harvest Fair, Dragonfly Street Faire, Marlborough Food Truck & Arts Festival, and Apple Fest at Longfellow’s Wayside Inn.
What historic fall events can you attend in MetroWest Massachusetts?
The Colonial Faire and Muster of Fife and Drum at Longfellow’s Wayside Inn in Sudbury offers a chance to experience colonial-era music, demonstrations, crafts, and traditions in a historic New England setting.
