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Sip, nibble and get in the holiday spirit at this weekend’s 9th Annual Cutchogue Holiday Stroll and House Tour. (Photo credit: Victoria Caruso)

The one constant thing you hear that the North Fork has over its South Fork sibling: the dreamy Main Road drive through all the towns is one charming setting after the next, all strung together like the beaded baubles on holiday garland. Still, there are a few towns that get the lion’s share of attention — Greenport, Southold and Riverhead arguably the areas that lure tourists and locals alike to shop, sup, sip and sightsee. But each of our towns has something special to offer, and that’s exactly what the Cutchogue Holiday Stroll and House Tour on Saturday, December 2, is set up to do.

The Old House is located on the Cutchogue Village Green. (Photo credit: Monique Singh-Roy)

“Cutchogue is a beautiful, vital town, but people think there’s not too much to offer in terms of shops,” says Lisa Sannino, one of the organizers of the Cutchogue Holiday Stroll. “But there are wonderful things here! And what we have are super into what they do!”

The event began nine years ago as a popular historical house tour and local business boost for the holiday season. The COVID 19 pandemic, though, altered the original blueprint of the event.

“It began as the Cutchogue Holiday House tour awhile back, but we took two years off with COVID. After that, a lot of homeowners didn’t feel comfortable opening their homes to 200 to 300 people,” says Sannino, who is co-owner of Sannino Vineyards and Sannino Vineyards Bed & Breakfast. “So we pivoted, like everything else in life. That’s when thought about a stroll instead.”

Highlighting the small businesses and their unique wares, the Holiday Stroll will bring participants from place to place for a bevy of holiday treats, music, unique gifts and even a tree lighting and visit from Santa.

Get cozy and comfy at Sannino’s Bed & Breakfast (seen here) and Blue Iris Bed & Breakfast. (Photo credit: Victoria Caruso)

The day starts at 11 a.m. on the Cutchogue Village Green, where participants check in and receive their Holiday Stroll tour map. From there, you can choose your own adventure — although we recommend you start with a visit to the Cutchogue-New Suffolk Historical Society’s Carriage House gift shop holiday pop-up, with all new holiday merch for the season, Old House, the glorious 17th century dwelling that’s a designated National Historical Landmark.

After your dose of history, this tiny town had a packed itinerary of fun that finishes back at the Green at 4 p.m. for the annual holiday tree lighting (accompanied by warm cider and cookies, of course!), a cascade of carols from a local chorus and an appearance from old Saint Nick himself.

Along the way, you can get an inside look at the area’s two lovely bed and breakfasts, Saninno and Blue Iris, each decked out in their best holiday decor for the season, and sips of the house wine at Sannino along with Little Fish noshes, and Pugliese Vineyard wine at Blue Iris, along with fun nibbles from a Mano restaurant to nosh on while you enjoy their comfy, cozy climes (and Sannino is providing a B&B shuttle to go between the duo of digs).

Savory and sweet bites to fuel your day-long stroll. (Photo credit: Victoria Caruso)

Art will be part of the day, too, at Borghese, who’s showcasing the work of local artists show along with wine from their historic vineyards, along with the Alex Ferrone Gallery, displaying thought-provoking work from the exhibition “Breathe” along with bites from The Catered Fork and sips from Pellegrini Vineyards.

You’ll also be able to check out the wares of the new North Fork French Picnic, NeyTiv Natural Spa, NOFO Wellness Center, Disset Chocolate (yum!), the Old Town Arts & Crafts Guild that Sannino lovingly describes as, “that little gift shop gift that keeps on giving — you walk in and it opens up to a world where all these artists have all their wares, from poetry to painting to cards — there’s a lot!”

And after all that, if you’d like to sit and swoon over what a lovely day you had, book a table at Touch of Venice for a special pocket-friendly $45 three-course dinner for attendees of the Holiday Stroll & House Tour (and the charms of Cutchogue, of course). When you check in for the Stroll, simply ask for the special prix fixe coupon for the cozy Italian eatery and present it when you show up for your dinner reservation that evening.

The whole day of delights is $75. Get your tickets from EventBrite here.