Looking for fall festivals, Halloween events, family activities, and seasonal fun in MetroWest Boston this October? From cider festivals and Oktoberfest celebrations to pumpkin walks, trick-or-treat events, live music, historic happenings, and glowing jack-o’-lanterns, there’s plenty to fill your calendar.
Here are some of the best October 2026 events happening across MetroWest Boston and nearby communities.
October Events at a Glance
October 1–4: Jack’s Abby Oktoberfest Weekend in Natick
October 3: Dragonfly Street Faire in Ashland, Framingham Fest, Oldtown Fall Fair in Natick, Apple Fest in Sudbury, Wayland Festival, and Phantoms by Firelight in Sturbridge
October 4: Cider Festival at Daniels Farmstead in Blackstone
October 12: Southborough Heritage Day
October 16: Holliston Oktoberfest
October 23: Jerusha’s Halloween Ball in Sudbury
October 24: Bellingham Halloween Trunk or Treat Stroll, Duck Soup 55th Anniversary Celebration, and Musicians of the Old Post Road in Sudbury
October 27: Westborough Main Street Trick or Treat
October 29: Downtown Hudson Trick or Treat
October 30: Medway Pumpkin Walk and Halloween Hullabaloo at Discovery Museum
October 31–November 1: Halloween Hullabaloo continues at Discovery Museum
Through November 1: The Great Jack O’Lantern Journey at Southwick’s Zoo
Acton
Halloween Hullabaloo at Discovery Museum
When: Friday, October 30, 10 a.m.–4 p.m.; Saturday, October 31, 10 a.m.–noon; Sunday, November 1, 10 a.m.–4 p.m.
Where: Discovery Museum, 177 Main Street, Acton
Celebrate Halloween weekend with family-friendly fun at Discovery Museum. Wear your costume and try Pumpkin Putt Putt, outdoor games with a Halloween twist, a Spooktacular Scavenger Hunt, and other seasonal surprises around the museum.
Some outdoor activities are weather-dependent, so check current event details before visiting.
Ashland
Dragonfly Street Faire
When: Saturday, October 3, 2026, from 1–6 p.m.
Where: The Corner Spot, 6 Cherry Street, Ashland
Spend an October afternoon in downtown Ashland at the Dragonfly Street Faire, featuring music, performers, food, beverages, and community fun at The Corner Spot.
Bellingham
Halloween Trunk or Treat Stroll
When: Saturday, October 24, 2026, from 5:30–7:30 p.m.
Where: Bellingham Town Common
Dress up the kids and head to the Bellingham Town Common for a festive Halloween Trunk or Treat Stroll. This community event offers an easy, family-friendly way to celebrate Halloween before the big night.
Blackstone
Cider Festival at Daniels Farmstead
When: Sunday, October 4, 2026, from 11 a.m.–3 p.m.
Where: Daniels Farmstead, 286 Mendon Street, Blackstone
Sip, savor, and celebrate fall at the annual Cider Festival at Daniels Farmstead. Visitors can enjoy hot cider, locally crafted hard cider, fresh baked goods, cider donuts, seasonal fare, live music, and the farm’s final weekly farmers market of the 2026 season.
The market also features locally grown produce, handmade goods, and products from local vendors. Admission to the festival and farmers market is free, with food and vendor purchases available separately.
Framingham
Framingham Fest
When: Saturday, October 3, 2026, from 11 a.m.–3 p.m.
Where: Framingham Centre Common
Celebrate the season with a community gathering at Framingham Centre Common featuring food, entertainment, and activities in the heart of Framingham.
Holliston
Oktoberfest
When: Friday, October 16, 2026, from 6:30–10 p.m.
Where: Holliston Historical Society
Enjoy an evening of German-inspired food, beer, wine, music, singing, and polka dancing at the Holliston Historical Society’s Oktoberfest celebration.
Hudson
Downtown Trick or Treat
When: Thursday, October 29, 2026
Where: Downtown Hudson, Main Street
Downtown Hudson transforms into a Halloween destination as local businesses welcome costumed children for trick-or-treating.
Participating businesses can be identified by pumpkins displayed in their windows, making it easy for families to stroll Main Street and collect treats along the way.
Medway
Pumpkin Walk
When: Friday, October 30, 2026, from 7–9 p.m.
Where: Choate Park, Medway
One of Medway’s favorite Halloween traditions returns with a nighttime walk through glowing carved pumpkins at Choate Park.
Pre-registration is required. Medway Community Farm will be on-site selling hot cocoa, popcorn, and snacks, and visitors are encouraged to bring flashlights because this is a dark event. Glow necklaces and bracelets will be provided.
A special 6:30 p.m. entry time is available for Medway residents with children under age 2.
Mendon
The Great Jack O’Lantern Journey at Southwick’s Zoo
When: Select evenings through November 1, 2026
Where: Southwick’s Zoo, Mendon
Step into a glowing Halloween world at The Great Jack O’Lantern Journey, one of the region’s biggest seasonal attractions.
The evening experience features illuminated carved pumpkins, live entertainment, seasonal treats, family activities, and spooky-but-family-friendly fun throughout the zoo. Southwick’s Zoo is also offering live Salem Sisters performances and other entertainment during the event.
Natick
Jack’s Abby Oktoberfest Weekend
When: Thursday, October 1–Sunday, October 4, 2026
Where: Jack’s Abby, Natick
Celebrate Oktoberfest all weekend long at Jack’s Abby. The festivities begin with a Thursday beer dinner, followed by Friday’s cask tapping, a Saturday street festival, and family- and dog-friendly fun on Sunday.
Expect live music, games, food, beer, and plenty of Bavarian-inspired celebration.
Oldtown Fall Fair for Natick’s 375th
When: Saturday, October 3, 2026
Where: Shaw Park, Natick
Celebrate Natick’s 375th anniversary with an afternoon of old-fashioned fall fun.
Try traditional games such as sticks and hoops and quoits, dig for treasure in the hay, explore local history, and enjoy music and other activities. At dusk, settle in with a blanket or lawn chair for an outdoor screening of The Goonies.
Southborough
Heritage Day
When: Monday, October 12, 2026, from 10 a.m.–1 p.m.
Where: St. Mark’s Field, Route 30 and Route 85 intersection, Southborough
Celebrate Southborough’s community and history at Heritage Day with a parade, artisan booths, food trucks, and activities throughout the morning and early afternoon.
Sturbridge
Phantoms by Firelight: Frankenstein Encounter
When: Fridays, Saturdays, and Sundays, October 3–25, 2026, from 4:30–9 p.m.
Where: Old Sturbridge Village, Sturbridge
As darkness falls over Old Sturbridge Village, the historic landscape transforms into the experimental world of Mary Shelley’s Frankenstein.
Rather than simply watching the story, guests walk through it as scenes unfold along lantern-lit paths throughout the 1830s village. The 2026 experience runs on 11 select nights in October.
Sudbury
Apple Fest at Longfellow’s Wayside Inn
When: Saturday, October 3, 2026, from 10 a.m.–2 p.m.
Where: Longfellow’s Wayside Inn, Sudbury
Celebrate autumn in a historic New England setting with music, food, a craft market, activities, and seasonal fun at Apple Fest.
Jerusha’s Halloween Ball
When: Friday, October 23, 2026, from 6–10 p.m.
Where: Longfellow’s Wayside Inn, Sudbury
For a grown-up Halloween night, head to Jerusha’s Halloween Ball.
The 21+ ticketed event features a pre-party tour of the Inn’s famously “haunted” Room 9, a costume contest, music, dancing, and plenty of Halloween atmosphere.
Duck Soup 55th Anniversary & Mill Village Fall Festival
When: Saturday, October 24, 2026, from noon–4 p.m.
Where: Mill Village, Sudbury
Celebrate 55 years of Duck Soup during the Mill Village Fall Festival, featuring music, games, treats, and community fun.
The celebration also includes a Goodnow Farms whisky pairing for visitors looking for an additional tasting experience.
Musicians of the Old Post Road: Playing it Forward
When: Saturday, October 24, 2026, at 4 p.m.
Where: First Parish, 327 Concord Road, Sudbury
Take a break from pumpkins and costumes for an afternoon of classical music.
Playing it Forward explores the musical relationships between teachers and students across generations, with works connected to composers including Handel, Bach, Haydn, Kirnberger, Goldberg, Anna Amalia, Porpora, and Marianna Martines.
Wayland
Wayland Festival
When: Saturday, October 3, 2026, from 10 a.m.–5 p.m.
Where: Wayland Town Center, 22 Andrew Avenue, Wayland
Spend the day at the Wayland Festival, featuring a multicultural pavilion, artists’ marketplace, Touch-a-Truck, food and beverage trucks, live music, and a parade celebrating the nation’s 250th birthday.
The 2026 festival is scheduled for October 3 from 10 a.m.–5 p.m. at Wayland Town Center.
Westborough
Main Street Trick or Treat
When: Tuesday, October 27, 2026, from 4–6:30 p.m.
Where: Downtown Westborough
Bring the kids downtown for Westborough’s annual Main Street Trick or Treat.
Participating businesses and municipal locations along Main Street, East Main Street, Milk Street, South Street, and surrounding downtown areas will hand out candy to trick-or-treaters. The event has grown into a popular community Halloween tradition attracting hundreds of families.
Plan Your October in MetroWest Boston
October in MetroWest Boston offers something for nearly every kind of fall outing. Families can explore pumpkin walks, trick-or-treat events, glowing jack-o’-lanterns, festivals, and outdoor celebrations, while adults can enjoy Oktoberfest gatherings, cider tastings, live music, historic events, and Halloween nights out.
Whether you’re looking for cozy daytime activities or spooky nighttime adventures, there are plenty of ways to celebrate fall throughout MetroWest Boston this October.
Be sure to check each event’s official website before heading out for the latest schedules, admission information, weather updates, and registration requirements.
Frequently Asked Questions About October Events in MetroWest Boston
What are some family-friendly Halloween events in MetroWest Boston?
Family-friendly Halloween events include Halloween Hullabaloo at Discovery Museum, the Medway Pumpkin Walk, Downtown Hudson Trick or Treat, Westborough Main Street Trick or Treat, Bellingham’s Trunk or Treat Stroll, and The Great Jack O’Lantern Journey at Southwick’s Zoo.
What fall festivals are happening in MetroWest Boston in October 2026?
October festivals include the Dragonfly Street Faire in Ashland, Cider Festival at Daniels Farmstead, Jack’s Abby Oktoberfest Weekend, Apple Fest at Longfellow’s Wayside Inn, the Wayland Festival, and Southborough Heritage Day.
Where can I see pumpkins and Halloween displays near Boston?
The Great Jack O’Lantern Journey at Southwick’s Zoo features illuminated carved pumpkins and entertainment, while Medway’s Pumpkin Walk offers a community display of carved pumpkins at Choate Park.
Are there Halloween events for adults in MetroWest Boston?
Yes. Adults can attend Jerusha’s Halloween Ball at Longfellow’s Wayside Inn, an age-21+ event featuring music, dancing, a costume contest, and a pre-party tour of the Inn’s “haunted” Room 9.
What are some October events that are not Halloween-themed?
Visitors can also enjoy Cider Festival at Daniels Farmstead, Wayland Festival, Southborough Heritage Day, Apple Fest, Oktoberfest celebrations, classical music performances, and community street fairs throughout the month.
