Port Jefferson's Fall Moves Up Main Street Before It Comes Back to the Harbor

East Main Street has eighteen scarecrows on it right now. One is a bowl of spaghetti and meatballs outside Pasta Pasta. One is a fishing scarecrow from Port Tackle. Another is Dolly Parton, from Tiger Lily. A Teen Wolf comes from the Port Jefferson Free Library Teen Center, and Scales of Justice comes from a law office. They went up on October 5 and stay until November 2. Anyone with an email address can vote for a favorite on the Greater Port Jefferson Chamber of Commerce's Scarecrow Walk page.

From October into early November, Port Jefferson's event calendar sits on the streets above the water. The Scarecrow Walk, the Fall Art Walk, the Harvest Festival and the Chowder Crawl all depend on businesses along Main Street, East Main and Mill Creek Road. Many of the same names show up in more than one event. The harbor takes over again on November 27, when the ice rink opens.

The October events are built out of storefronts

Every Scarecrow Walk entry is tied to a local business or organization. The 2026 list includes Huntington Learning Center, Long Island Mental Health Services, The Wellness Stop, Coolsmiles, HighCs Voice Studio, Nicole Palumbo Law, P.C., WILD Plant Shop, Harmony & Light Wellness, Dark Horse Coffee & Kitchen, Tea Brew, Lavender Fields, Shades of Beauty, North Shore Hair Co and PJ Vintage, along with the ones above. The walk reads like a directory of East Main Street that happens to have hay in it.

The self-guided Fall Art Walk works the same way. It runs October 9 through November 6. The Chamber says printed guides will be available at participating businesses, the Chamber office and the PJ Village Center. The artist sign-up rules said each piece goes in a business's front window, and the Chamber assigns placements to match each artwork with a business. Artists had to be over 18. Entry cost $15 for one piece or $40 for three, and registration closed September 24. The Chamber's web page doesn't list which artists landed in which windows, so a printed guide from one of those pickup spots is the way to plan a route.

The two walks overlap for almost four weeks. Between October 9 and November 2, one stroll along East Main can take in scarecrows on the sidewalk and art in the windows behind them.

Harvest Festival weekend covers four addresses

The Harvest Festival runs Saturday, October 17 and Sunday, October 18. The Chamber hosts it with local community groups and businesses. It doesn't happen on one festival ground. The activities are spread across the village.

Here's the layout from the Chamber's activity-pass page, roughly in walking order:

1. Information table, Mill Creek Road. Pick up wristbands here, near the Harvest Photo Op. Bring your purchase confirmation or the name on the order. Passes are also sold here during the festival, for cash or online.
2. Inflatable axe throwing, Mill Creek Road, 1 to 4 p.m. It's on the same street as the info table.
3. Inflatable corn maze, Tommy's Place parking lot at 109 Main Street, 1 to 4 p.m.
4. Pumpkin patch, Park at 114 at the Port Jeff Library, 110 Thompson St., 1 to 5 p.m. One pumpkin per person. Peter's Fruit Company and Castaways Steak & Seafood sponsor it.
5. Tractor hay ride from Harborview Christian Church, 315 E. Main St., 1 to 5 p.m. The ride loops through Port Jefferson Village.

A $15 pass covers all four activities for one day, and four passes cost $45. You choose the day when you buy, and a Saturday pass won't work on Sunday. No refunds. Single entry to any one activity is $5, and the pumpkin patch price includes a pumpkin. You show your wristband at each stop. A family of four buying single entries for every activity would pay $80. The four-pass bundle is $45.

The axe throwing and corn maze close an hour before the hay ride and pumpkin patch. A family arriving after 3 p.m. has a tight window for those two. The Chamber's festival page also promotes a pie-baking contest and "Hugh Stinkfoot and the Spooky Terrible Day!" along with the Scarecrow and Art Walks. The full timed schedule is posted only as image flyers, so check those for performance times.

The Chowder Crawl puts a dozen dining rooms on one ticket

The following Saturday, October 24, the Chowder Crawl runs from noon to 3 p.m. The Chamber's crawl listing names twelve participating restaurants:

• Barito Tacos & Cocktails
• Castaways Steak & Seafood
• Curry Club at SaGhar
• Dark Horse Coffee & Kitchen
• Ditch
• La Cova
• Pasta Pasta
• PJ Lobster House
• Nantuckets
• The Canopy Club
• The Steam Room
• Tommy's Place

Tickets are $30 through the Chamber's Zeffy page. Each ticket is a booklet that you show at each restaurant to get your chowder. Ticket holders get a notice when booklets are ready for pickup and need to bring their Zeffy receipt. Tickets can't be refunded. To vote, scan the QR code on your ticket or at a participating restaurant. As of this writing, the Chamber's event page still lists its own voting form as "coming soon."

The crawl is where the October overlap shows most. Pasta Pasta and Dark Horse Coffee & Kitchen have scarecrows on East Main and are also pouring chowder. Tommy's Place hosts the corn maze in its lot one weekend and serves chowder the next. Castaways sponsors the pumpkin patch and is on the crawl too. Shades of Beauty, another scarecrow entry, marked one year at 464 Main St. on September 29. TBR News Media reported that owners Kathy Lee and Steve Engels are expanding the salon into two storefronts.

November 27: the calendar returns to the water

Things start heading back downhill once the Scarecrow Walk ends on November 2 and the Art Walk on November 6. The Village calendar lists Friday, November 27, 2026, as opening day for outdoor ice skating at the Village Center. It says the Rinx at Harborfront Park will stay open through March 14, 2027. The Village gives the address as 101A Robert T. Strong Way. The Rinx's own site uses 101-A East Broadway.

The Rinx's public skating page currently shows these prices. The page isn't dated and says the schedule and rates can change without notice.

Weekday sessions currently run at noon, 2, 4 and 6:30 p.m. Friday and Saturday add an 8-to-10 p.m. night session, and weekend mornings start at 10.

The Village Center may also have a food option this winter. Patch reported on October 6 that the Village was taking proposals for a winter refreshments concession there, with bids due October 13. No operator had been named.

The Chamber lists the Festival of Trees at the Port Jefferson Village Center from December 1 to January 2. The 30th Annual Charles Dickens Festival is on the Village calendar for Saturday, December 5 and Sunday, December 6.

Whether you're saving a chowder booklet spot for out-of-town guests or wondering how a busy event weekend on Main Street fits around a showing or an open house, Conor Hertell can walk you through the timing on your block. Buy or sell? Call Hertell today.