🍎🍂 2026 North Shore Fall Festival Guide
Family-Friendly Fall Fun from Amesbury to Cape Ann
There’s something special about fall on the North Shore — apple cider donuts, pumpkins, crisp ocean air, harvest celebrations, corn mazes, local makers, live music, and plenty of reasons to spend a weekend outside with the kids.
Here are some of the 2026 fall festivals and seasonal celebrations to put on your family calendar. I focused on Amesbury, Newbury, West Newbury, Newburyport, Rowley, Ipswich, Essex, Manchester-by-the-Sea, Hamilton, Wenham, Rockport, and Gloucester. Some towns have not yet announced their full 2026 fall calendars, so I’ve noted that rather than filling in unconfirmed dates.
As always, dates and details can change, so check the event website before heading out.
🍎 AMESBURY
Fall at Cider Hill Farm
•Farm•Open••
📍 45 Fern Avenue, Amesbury
Cider Hill Farm is one of our favorite places to welcome fall. The 145-acre family farm offers plenty of reasons to visit during harvest season, including pick-your-own fruit, the farm store and bakery, family play areas, seasonal treats and activities.
Fall weekends can get particularly busy, so families looking for a quieter experience may want to consider a weekday visit.
🍎 Look for apple picking and harvest activities
🍩 Grab some cider donuts and other bakery treats
🎃 Watch for pumpkins and other seasonal offerings
👨👩👧👦 Great for a full family fall outing
Cider Hill Farm Festivals & Events
🌽 Corn Festival
August 22–23, 2026
For families who just can't wait until September to start celebrating harvest season, Massachusetts' 2026 event calendar lists a Corn Festival in Amesbury August 22–23.
🍎 WEST NEWBURY
37th Annual Apple Harvest Run & Fall Celebration
📅 Sunday, October 18, 2026
📍 15 Bachelor Street, West Newbury
This is much more than a road race!
The annual Apple Harvest Run benefits the Dr. John C. Page Elementary School and includes a 1-mile kids' fun run, 5K and 5-mile race. Afterward, families can stick around for a fall carnival and community celebration.
The festivities are scheduled to include:
🍎 Family activities
🏰 Bounce house
🎯 Obstacle course and games
🎁 Prizes
🛍️ Community vendors and young entrepreneurs
🎪 Carnival fun
The 1-mile fun run begins at 11 a.m., followed by the 5K and 5-mile races at 11:30 a.m.
Apple Harvest Run Information & Registration
🍂 NEWBURYPORT
Newburyport really embraces autumn, with several annual events on the city's cultural calendar.
🍎 Newburyport Fall Harvest Festival
The city's annual cultural-events calendar lists the Fall Harvest Festival in October, one of Newburyport's signature autumn traditions.
Think downtown Newburyport in peak fall mode — shopping, strolling, food, entertainment and a great excuse for a family day downtown.
The exact 2026 date has not yet been posted on the city calendar I found, so I'd hold off on putting a specific date in your family calendar just yet.
Newburyport Annual Cultural Events
🎃 Pumpkin Lighting
Also returning to Newburyport's annual October calendar is the city's Pumpkin Lighting.
This is another one to watch as the full 2026 schedule is released.
🌽 IPSWICH
Fall Fun at Marini Farm Corn Maze
•Park•Closed••
📍 255 Linebrook Road, Ipswich
While technically more of a seasonal attraction than a one-day festival, Marini Farm deserves a spot in a North Shore family fall guide.
The farm's seasonal corn maze is paired with a maze park and other family activities, making it an easy place to spend several hours enjoying classic New England fall fun.
🌽 Corn maze
🎃 Fall atmosphere
👧 Children's activities
🍂 Maze park
🍎 Farm treats and seasonal fun
The attraction operates seasonally, so check the farm's current calendar and ticket information before visiting.
🎃 ROCKPORT
🍎 Rockport Harvest Fest
📅 Saturday, October 17, 2026
⏰ 11 a.m.–5 p.m.
🌧️ Rain date: Sunday, October 18
📍 Downtown Rockport
💰 FREE
This may be one of the best family fall day trips on the list.
Rockport combines its gorgeous seaside setting with a traditional harvest celebration throughout downtown. The Greater Cape Ann Chamber describes the day as a mix of local harvest traditions and coastal charm.
Families can expect:
🎶 Local musicians and entertainment
🛍️ Artisan and local vendors
🎨 Seasonal children's crafts
🎨 Face painting
🐢 Live animal exhibit
🍎 Apple Pie Bake-Off
🎯 Lawn games
🍴 Seasonal food
🛍️ Downtown shopping
And yes — you can celebrate fall while looking at the ocean. That's about as North Shore as it gets.
Rockport Harvest Fest 2026 Details
⚓ GLOUCESTER
⛵ 42nd Annual Gloucester Schooner Festival
📅 September 4–6, 2026
📍 Gloucester Harbor
Labor Day weekend brings one of Gloucester's signature celebrations back to the harbor.
The 42nd Annual Gloucester Schooner Festival brings historic schooners from near and far to Gloucester for a weekend celebrating the city's maritime heritage.
Activities are expected to include:
⛵ Schooners throughout Gloucester Harbor
⚓ Deck tours
⛵ Parade of Sail
🏆 Mayor's Cup Races
🎆 Festival festivities
🌊 Plenty of waterfront activity
It's an especially fun choice for kids who love boats.
Official Gloucester Schooner Festival 2026
🎨 Cape Ann Plein Air
📅 October 3–11, 2026
For families with budding artists, Cape Ann Plein Air brings 36 juried artists to Cape Ann to paint the area's coastal landscapes. The week includes artists working throughout the area and culminates in competition and related activities.
It's a different kind of fall festival experience — and a wonderful way to introduce kids to art while exploring Cape Ann during one of the prettiest times of year.
🍂 Make a Fall Bucket List!
There are enough celebrations on the North Shore to turn September and October into one long family fall adventure. Pick apples in Amesbury, run and play at West Newbury's Apple Harvest celebration, wander downtown Newburyport, tackle a corn maze in Ipswich, watch schooners sail through Gloucester Harbor, and finish the season surrounded by pumpkins, music and ocean views at Rockport Harvest Fest.
Macaroni KID Tip: Bookmark this guide! Many towns, libraries, farms and community organizations haven't released their complete September and October 2026 calendars yet. We'll continue adding festivals, pumpkin celebrations, Halloween events and harvest activities as they're announced.
Event details were researched as of August 18, 2026. Always confirm dates, times, admission and weather policies directly with the organizer before heading out.
