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Wickham's Fruit Farm

Apples at Wickham’s Fruit Farm in Cutchogue. (Credit: David Benthal)

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Pumpkin picking might be synonymous with October on the North Fork, but there is so much more to do here during the fall.

From festivals and mid-week dinner deals to haunted houses, here are 31 events to check out — one for each day of the month. As always, visit for even more listings.

Sunday, Oct. 1

Elvis Night at Porto Bello

Elvis will re-enter the building. Impersonator Paul Monroe will perform at the Greenport restaurant at 6 p.m. The $50 ticket includes dinner and dessert.

1410 Manhanset Avenue, Greenport, (631) 477-1515,

Monday, Oct. 2

Drink Long Ireland Okoberfest

Beer writer B.J. Gamboa recently penned a post for us on ways to celebrate Oktoberfest on the North Fork. One of his recommended local brews was the Oktoberfest from Long Ireland. Give it a taste!

817 Pulaski Street, Riverhead, (631) 403-4303,

Tuesday, Oct. 3

Fall Pumpkin Picking

Get your gourds at a number of North Fork farms on a day when the roads and fields will be less crowded. Click here for a list of U-pick options.

Wednesday, Oct. 4

Wednesday Night Trivia Greenport Harbor Brewery

The popular brewery’s Peconic location will host a trivia contest with signup beginning at 5:15 p.m. Winners receive a $50 gift card to the brewery.

42155 Main Road, Peconic, (631) 477-1100,

Thursday, Oct. 5

World Teacher’s Day at Andy’s

One of Greenport’s newest restaurants is hosting a special happy hour for all school employees on this unofficial holiday. Check it out from 4 to 7 p.m.

34 Front Street, Greenport, (631) 333-2525,

Friday, Oct. 6

First Fridays on Love Lane

You can’t miss the final First Fridays of 2017. Enjoy food and drinks at this popular Mattituck street fair.

Participating local businesses will offer special discounts, demonstrations or giveaways in their stores all day. The event runs from 6 to 9 p.m.

Love Lane, Mattituck,


The Garden Conservancy Open Days

Saturday, Oct. 7

Open Days Garden Tour

Explore two private gardens in Cutchogue and Shelter Island with self-guided tours to benefit the Garden Conservancy. Highlights include bayfront views, a park-like woodland garden, numerous specimen evergreens, antique and salvaged garden ornaments and native plants for supporting wildlife and testing for deer resistance. Admission is $7 per garden; children 12 & under free.

4560 Vanston Road, Cutchogue and 3A Wesley Avenue, Shelter Island, 1-888-842-2442,

Sunday, Oct. 8

Riverhead Country Fair

Experience this historic carnival with a fall theme, featuring pumpkin decorating and carving contests. The fair runs from 10 a.m. from 5 p.m. but you need to arrive between 7 and 9 a.m. if you’d like to enter the contests.

Peconic Riverfront, 631-722-3873,


Monday, Oct. 9

Lieb Cellars Harvest Party

This Oregon Road winery is hosing two harvest party sessions at 1 and 3 p.m. featuring flights and small bites, live music and a “good old-fashioned grape stomp.”

13050 Oregon Road, Cutchogue, (631) 734-1100,

Tuesday, Oct. 10

Wednesday, Oct. 11

Italian Wine and Cheese tasting

Michael Affatato of the Village Cheese Shop is serving up Italian wine with European cheese at the Cutchogue New Suffolk Library from 6:30 to 7:30 p.m. He’ll also share stories from his travels, and his experience and expertise in the industry. This event is just $10.

27550 Main Road, Cutchogue, (631) 734-6360,

Thursday, Oct. 12

Lenz Goes to Brooklyn

Live the North Fork life in Park Slope when The Lenz Winery serves up a four-course progressive wine dinner at  four different eateries in an event sponsored by Edible Brooklyn. Dessert further bridges the gap between the North Fork and Brooklyn with Four & Twenty Blackbirds pie. It’s $125 per person and features 6:30 and 7:30 p.m. seatings.

Park Slope, Brooklyn,

Friday, Oct. 13

Martha Clara Merlot Masquerade

Have a ball — masquerade style — in the Martha Clara Pavilion from 7 to 10 p.m. Masks will be provided to complement cocktail attire. Tickets include passed hors d’oeuvres and two complimentary glasses of wine for $85 ($65 for wine club members).

6025 Sound Avenue, Riverhead, (631) 298-0075,

Saturday, Oct. 14

Pindar Vineyards Rock the Harvest

Rock the Harvest returns with the Montauk band Hopefully Forgiven. Celebrate harvest season with wine from the Peconic winery and Forks BBQ. Admission is free and the party starts at noon.

37645 Main Road, Peconic, (631) 734-6200,


Sunday, Oct. 15

Brunch on the bay

Peconic Cruise Line teams up with Grace and Grit to offer “Brunch on the Bay.” The meal includes a complimentary bloody mary, North Fork Roasting Co. coffee, juice and a menu from Grace and Grit caterers in Southold. Tickets are $50, for general admission, $45 for seniors and $35 for children 12 and under. The two-hour cruise runs from 9:30 a.m. until 11:30 a.m.

Click here for tickets.

Peconic Cruise Line, Railroad Dock at the foot of 3rd St., Greenport, (631) 901-7899

Monday, Oct. 16

Make a local dinner at home

Stop into Sang Lee Farms in Peconic to pick up ingredients for an all-organic fall dinner. Local butternut squash makes for an excellent The farm will be open noon to 5 p.m. Mondays through Thursdays this fall and 9 a.m. to 5 p.m. Friday, Saturday and Sunday.

Sang Lee Farms, 25180 Route 48, Peconic, (631) 734-7001


Tuesday, Oct. 17

Elbow Room happy hour

Cliff’s Elbow Room in Jamesport offers a happy hour specials weekdays from 4 p.m. until 7 p.m. Half price appetizers with beer and drink specials.

Cliff’s Elbow Room, 1549 Main Rd., Jamesport, (631) 722-3292

Wednesday, Oct. 18

Wednesday night Shucker Club

Are you an oyster fan? Then the Wednesday Night Shuckers Club at Little Creek Oysters is for you. This event is held every Wednesday night from 5 to 8 p.m. with $5 Greenport Harbor beer, U-shuck specials and shucked oyster specials.

Little Creek Oyster Farm and Market, 37 Front Street, Greenport, (631) 477-6992

Phil's Waterfront Aquebogue

Thursday, Oct. 19

Football at Phil’s

Head to Phil’s to watch Thursday night football, which features a marquee matchup between the Chiefs and their rival Raiders on this night. Half-priced apps at he bar during NFL games.

Phil’s Waterfront Bar & Grill, 177 Meeting House Creek Rd., Aquebogue, (631) 886-1160

Friday, Oct. 20

Ha Ha Halloween

Long Island Comedy presents Ha Ha Halloween at Suffolk Theater in Riverhead. Comedians Paul Anthony, John Santo, Banjo Les and Maureen Langan will performs. Doors open at 6:30 p.m. and the show starts at 8 p.m. Pre-sale tickets are $25. Click here to purchase them.

Suffolk Theater, 118 E. Main St., Riverhead, (631) 727-4343

Saturday, Oct. 21

5K in support of breast cancer research

Proceeds from the Shelter Island 5K support North Fork Breast Coalition, the Coalition for Women’s Breast Health at Southampton Hospital and Lucia’s Angels. Medals awarded. Dogs and strollers welcome. Free shuttle bus from North Ferry to registration runs between 9 and 10:15 a.m.; return shuttle runs until 1 p.m. First 500 participants guaranteed race shirts and goody bags.

Race starts at 11 a.m.

Free post-race barbecue. Registration (prior to midnight, Oct. 20): $30; kids 14 and under, $10; same-day registration: $40; kids 14 and under, $20.

Shelter Island Fall 5K, Crescent Beach, Shelter Island

Sunday, Oct. 22

Fall Festival at Gabrielsen’s

Rides, bounce houses, farm animals, pumpkin picking, roasted corn and their greenhouse-grown hardy mums, Montauk daisies and ornamental cabbage and kale. Admission to Gabrielsen’s Country Farm Fall Festival is $5 for adults and $9.95 for children on both weekends and weekdays. Live music and hay rides are only available on weekends and begin Sept. 16. The farm is open from 8 a.m. until 6:30 p.m. every day and the festival runs through Oct. 31.

Gabrielsen’s Country Farm, 200 Herricks Lane, Jamesport, (631) 722-3259

Monday, Oct. 23

Take a barre class

Drop in for a class at The Barre Room. Monday classes are 8 a.m., 1 p.m. and 2 p.m. (stretch). Barre classes are $15 and stretch are $10. Visit for more details.

The Barre Room, 445 Pike St., Mattituck, (917) 697-2092


Tuesday, Oct. 24

Meditation at The Giving Room

Start your morning off right with meditation at The Giving Room in Southold. Open sessions begin at 10 a.m.

The Giving Room, 56215 Main Rd., Southold, (631) 765-6670

Wednesday, Oct. 25

Cheese, please

Cheese is the perfect mid-week pick me up. Stop into the Village Cheese Shop in Mattituck and pick up some Humboldt Fog or some Catapano Dairy Farm chevre and have an after dinner nibble.

Village Cheese Shop, 105 Love Lane, Mattituck, (631) 298-8556

Thursday, Oct. 26

Date night at Cooperage Inn

Two salads, two entrées and a bottle of wine are $58. Reservations are recommended.

Cooperage Inn, 2218 Sound Ave., Calverton, (631) 727-8994

Friday, Oct. 27

Halloween masquerade at Long Island Aquarium

Wear a costume or grab a mask for our Halloween Masquerade Ball for adults.  Includes open bar, DJ, passed hors d’ouevers and light buffet. The party runs from 8 p.m. until midnight.

Tickets are $69.95. Call for more information.

Long Island Aquarium, 431 East Main St., Riverhead, (631) 208-9200

Saturday, Oct. 28

Halloween party at Pace’s Dockside

Music provided by That Motown Band. Costume contest with food and drink specials. Call for more information.

Pace’s Dockside, 2255 Wickham Ave., Mattituck, (631) 315-5252

Long Beach Bar “Bug” Lighthouse. (Credit: Katharine Schroeder)


Sunday, Oct. 29

Bug Light Halloween family cruise

Long Beach Bar “Bug” Lighthouse will be decked in ghoulish decor for this family-friendly event. Explore the lighthouse, join in the games, listen to lighthouse ghost stories, participate in the costume contest, enjoy cider and snacks.

Tickets are $25 for adults and $10 fro children ages 3 to 15. The tour runs from 4 p.m. until 6 p.m. Click here to purchase tickets.

East End Seaport Museum, 103 3rd St., Greenport, (631) 477-2100

Monday, Oct. 30

Pick up cider at Wickham’s Fruit Farm

Few beverages are tastier — or more seasonably appropriate — than the apple cider at Wickham’s Fruit Farm. This centuries old Cutchogue farm uses a cider press that’s more than 100 years old and is the oldest in New York State.

28700 Main Road, Cutchogue, (631) 734-6441,

Tuesday, Oct. 31

A Halloween Haunted House visit

One of the most popular haunted attractions in the country — according to BuzzFeed, anyway — is located right in our backyard. Darkside Haunted House is open from 7 to 11 p.m. on Halloween. Admission is $25.

Darkside Haunted House, 5184 Route 25A, Wading River, (631) 369-7227