13 Ways to Have the Best Week This October

Here it is again, that in-between month where it’s not quite hot enough for shorts, but definitely not cold enough for a winter coat. There’s plenty of love for this betwixt time of year, and not just because it gives us an excuse to dress in costume and go to parties. Fall foliage is the perfect backdrop for scheduling in The Best Week!

Have a decadently anti-social moment by the fire. Relish in a speakeasy-friendly Sidecar, pour a vintage-inspired Aphrodite and pen precious memories in a devilish grown up Christian Lacroix journal.

Have a night out in Chelsea at Sleep No More at The McKittrick Hotel. Since you won’t be sleeping, you’ll need to “…drink to the general joy o’ the whole table” at the affiliated rooftop bar Gallow Green.

Need to get the golf game going? Rock Hill Golf and Country Club in Manorville is where players of all levels strive for excellence (meet the pro and get On Par). After tee time, cruise over to PeraBell Food Bar’s second location in Riverhead for a well-deserved cold brew.

Take advantage of the season by jumping in the Leaf Pile (Ale). Greenport Harbor is where arts and crafts lovers “live deep(er)” while sipping ale dressed in labels created by local artists and listening to live music. Keep the vibe alive in Greenport with a visit to The South Street Gallery to view works from emerging artists.

Cover story, and hometown boy, Chris Wingert makes good on the small screen with his New York City Football Club. Catch him and other MLS stars pressing high on one of the many televisions at Prost Grill & Garten in Garden City.

Bike the spy trail and embrace the sketchy past of the area—a peek through the windows of the Spy Museum are recommended if you can find it. For more promising peeping, Local Color: Then and Now is on view at Gallery North in East Setauket. After the exhibit, enjoy an artisanal Italian dinner at Pentimento in Stony Brook.

Take a leisurely drive along the North Fork on Main Road. Farm fare and pastoral scenes will melt the week’s stress away. End the tour by rewarding your palate with flights of wine and live music at Raphael Vineyards.