What's Happening on the North Shore This Weekend: September 26-27, 2026

It is a big late-September weekend on the North Shore, Massachusetts. The 22nd Newburyport Documentary Film Festival fills the Port with three days of films, Salem's spooky season officially gets underway with the opening of the Haunted Happenings Marketplace, and in between there is a farmers market, a Sunday half marathon, live blues, oysters, and plenty of quiet coastal walks. Here is Kathleen's guide to the verified highlights, town by town, for the weekend of September 26-27, 2026, with admission, parking, and MBTA notes where they help.

The 22nd Newburyport Documentary Film Festival anchors the weekend, Friday September 25 through Sunday September 27, screening roughly 35 films across two venues: the Firehouse Center for the Arts at 1 Market Square and the Newburyport Screening Room at 82 State Street. Opening night Friday runs 6:30 to 10:00 PM at the Firehouse with a reception and the showcase film, a filmmaker Q&A, and an after-party at Loretta's Restaurant. Saturday brings daytime film blocks and evening showcases at both venues. Festival passes and individual tickets are available through the festival at nbptdocufest.org, and Saturday showings sell out, so book ahead.

Oysterfest in the Port returns Saturday September 26 from 1:00 to 5:00 PM at the Tannery Marketplace, behind Building #5 at 75 Water Street. Now in its sixth year, it is hosted by Newburyport FISH. One honest note: it is a ticketed event, not free admission. The ticket includes entry, a dozen oysters for tasting, and other oyster-adjacent tastings with live music; the full experience runs about $100 and tickets are sold through the event's Eventbrite listing.

Saturday also brings the Brett Burkinshaw Memorial Scholarship Fund Cornhole Tournament at 1:00 PM at the Newburyport Elks, 25 Low Street, a fundraiser honoring a fallen Newburyport firefighter. Sunday morning, the PortRun Half Marathon and 5K starts at 8:00 AM from RiverWalk Brewing, with registration and fees through the race's website.

Getting there: downtown parking is metered and fills early on event weekends, so arrive before mid-morning or take the train. Newburyport station on the Newburyport/Rockport Commuter Rail line is a short walk from downtown. Explore Newburyport real estate and living in the full community guide.

Salem's Halloween season kicks off in earnest this weekend. 2026 is Salem's 400th anniversary year and Halloween falls on a Saturday, so the city expects heavy crowds; plan transportation ahead. The Haunted Happenings Marketplace opens Saturday September 26 across downtown locations including Salem Common, Derby Square, Charlotte Forten Park, and Essex Street, roughly 10:00 AM to 8:00 PM, with local vendors and crafts to browse.

The Making of a Witch, a Play in One Act runs Saturdays at 2:00 PM, including September 26, at St. Peter's-San Pedro Episcopal Church, 24 St. Peter Street. The 35-minute play tells how Philip English, the wealthy Salem merchant, became an accused witch and escaped the trials. Tickets have run around $20 in prior seasons, and proceeds support the church.

Hollowed Harvest returns for its sixth season at 300 Derby Street: an all-ages, non-scary walk-through labyrinth of carved and animated jack-o'-lanterns with hands-on pumpkin carving. It runs through the Halloween season and requires a ticket, so check hollowedharvest.com for the day's hours.

For something hands-on, the Slime Potion Brewing Class at The Lost Library, a peculiar gift shop inside Salem Wax, runs Saturday sessions from 10:00 to 11:30 AM at 282 Derby Street, with tickets around $20 through the Salem Wax Museum.

The weekend kicks off Friday night with Mayor's Night Out, 5:00 to 7:00 PM: downtown trick-or-treating, free admission to participating museums for Salem residents with photo ID, merchant specials, and free parking after 2:00 PM at two downtown garages for residents. It is one of the signature events of the city's 400th anniversary year.

Getting there: Salem station on the Newburyport/Rockport line is a few blocks from downtown, and it is the smart move on an October-season weekend, when parking is scarce. Explore Salem real estate and living in the full community guide.

Guitar Monsters: Ana Popovic, Dance to the Rhythm Tour with Danielle Miraglia plays The Cut, 177 Main Street, on Saturday September 26. Doors open at 7:00 PM, the show starts at 8:00 PM, and it is an 18+ show: general admission standing starts around $39.50 plus fees, with seated tiers above that. It is general admission, so arriving early is worth it.

Gloucester pairs a working harbor with an artist's light. Hammond Castle Museum on Hesperus Avenue is a favorite sightseeing stop; confirm current weekend tour hours on its website before you go.

Getting there: Gloucester station and West Gloucester station on the Rockport branch of the Newburyport/Rockport line both serve the city, and The Cut is a short walk from the Gloucester station. Explore Gloucester real estate and living in the full community guide.

The Rockport Farmers Market continues Saturdays from 9:00 AM to 1:00 PM at Harvey Park, at the corner of Broadway and Mount Pleasant Street, through October 10. It is free to browse, with local produce, baked goods, maple syrup, flowers, and crafts, and it runs SNAP matching. Pair it with a walk along Bearskin Neck, where the galleries and shops are open for the shoulder season.

Getting there: Rockport station is the terminus of the Rockport branch, and Harvey Park is a short walk from the station. Explore Rockport real estate and living in the full community guide.

Express Yourself, Bloom, a free pop-up exhibition of artwork created by the youth of the Boch Center's BLOOM performance, is on view at the Carol Grillo Gallery, 406 Hale Street, in Endicott College's Manninen Center for the Arts. It runs from late September into early October and is open daily from 10:00 AM to 4:00 PM, which makes it an easy stop on a coastal Saturday.

Getting there: Beverly Depot is the junction of the Newburyport and Rockport branches, and downtown Beverly has metered street parking and municipal lots a short walk from the gallery. Explore Beverly real estate and living in the full community guide.

The Lynn Brews, Views, Bites & Beats Festival returns Saturday September 26 to the Lynn Ferry Terminal on Blossom Street Pier. General admission runs 12:00 to 6:00 PM for $7, with a VIP hour at 11:00 AM; the lineup includes food trucks, craft brews, live music, and an artisan market. Event parking is directed to the lot at 330 Lynnway.

The Dudes Trio plays a community party at the Lynn Ferry landing Saturday from 2:00 to 4:00 PM, free to the public.

Getting there: Lynn Interim station on the Newburyport/Rockport line serves downtown; the ferry terminal is on the waterfront, about a mile from the station. Explore Lynn real estate and living in the full community guide.

How to Read Tarot: A Beginner's Workshop takes place Saturday September 26 at Willowdale Bookshop, 169 Main Street, with a $55 workshop fee. Pre-registration is required; the shop posts event details on its website and can be reached at (978) 233-1167.

Getting there: Rowley station on the Newburyport branch is the town's rail stop, and the bookshop is in Rowley center, a few minutes from the station by car. Explore Rowley real estate and living in the full community guide.

No major scheduled public events in Newbury itself this weekend; PlumFest took place earlier in the month, on September 12. That makes Plum Island a perfect quiet-day stop, with walking and birding at the Parker River National Wildlife Refuge. One honest heads-up: from May through September the refuge's roughly 350-vehicle parking fills on most weekends, and the refuge closes to vehicles when full, so arrive early and check fws.gov for current alerts.

Getting there: Newbury has no train station; the closest stops are Newburyport and Rowley on the Newburyport branch. Plum Island is reached by car over the Plum Island Turnpike bridge. Explore Newbury real estate and living in the full community guide.

The quieter option this weekend. Castle Hill on the Crane Estate, Crane Beach, and Appleton Farms are classic late-September stops; check the Trustees of Reservations website for the day's hours and any garden programming before you head out. The big Ipswich Illumination fall festival is still a couple of weekends out, on October 10.

Getting there: Ipswich station on the Newburyport branch is about a mile from the town center, with the Crane Estate and Crane Beach a few minutes beyond by car. Explore Ipswich real estate and living in the full community guide.

No large public events found for Essex this weekend. It is a lovely weekend for a riverfront walk, antiquing and dining on Main Street, and a stop at the Essex Shipbuilding Museum if its hours suit. Check with local operators for the day's schedule.

Getting there: Essex has no train station; the closest stops are Gloucester on the Rockport branch or Ipswich on the Newburyport branch, each a short drive away. Parking clusters around Main Street and the river. Explore Essex real estate and living in the full community guide.

Two live shows anchor the beach on Saturday. Comedian Bob Marley plays Salvatore's at Riverwalk, with tickets through the venue. And Blue Ocean Music Hall hosts Beatlejuice, a Beatles tribute band, Saturday at 8:00 PM with doors at 7:00 PM; tickets are through the venue.

Getting there: Salisbury has no train station, so plan to drive; the closest MBTA rail stop is Newburyport, a short drive south. Explore Salisbury real estate and living in the full community guide.

• Book Newburyport Docu Fest passes and Oysterfest tickets ahead; both sell out, and Saturday showings fill first.

• Salem will be busy all October: go early for the Marketplace and the slime class, and let the Commuter Rail do the parking for you if you can.

• The Rockport market, the Beverly exhibit, and the Dudes Trio set at the Lynn ferry landing are all free, easy stops.

• Parker River Refuge parking fills early in the day; arrive before mid-morning and check fws.gov for alerts.

• Late-September schedules can shift, so glance at venue websites the morning of.

The North Shore runs on a year-round rhythm, and each town in this guide wears the seasons differently: summer crowds give way to fall festivals, quiet winters, then the slow build toward another summer. Since 2003 I have helped buyers and sellers across these communities find their next move, and I know which town matches which way of living. Whenever you want to talk through what makes sense for you, call (978) 500-1480 or book a consultation.