We’re headed to Montauk for the long weekend to visit with family — my niece and nephews, who I haven’t seen in five months, are up visiting from Florida! But if you don’t have plans, I have some ideas for you. Pack a bag and head out of town to…
The North Fork, Long Island
Only an hour and a half jaunt east on the Long Island Expressway, you’ll be smack dab in the heart of pumpkin picking country. We spend our summers out here, so you’ve probably heard me talk about it before, but the NoFo is a great destination for families. Kids will love the “frontier-town” festivities at Harbes Farm (think: pig racing), and parents will love a stop at one of the dozens of wineries. There aren’t that many places to stay on the North Fork, but we can recommend clean and reasonable accommodations in South Jamesport at the Jamesport Bay Suites (waterfront) and the Duncan Inn (recently renovated and on the main drag); as of pub time, both had some availability for Columbus Day weekend. If you go, print out our day trip to the North Fork guide we published a few years back. (AND if you can snag a dinner or brunch reservation at the Jedediah Hawkins Inn, shown above, it’s not to be missed!)
Watch Hill Inn, Rhode Island
I’ve been dreaming about staying in this gorgeous hotel on the water in Watch Hill, Rhode Island for years, but boy is it a splurge! Still, I bet it’s worth every penny — and they have rooms this weekend! Located directly on the harbor, Watch Hill is a Victorian village about fifteen miles east of Mystic, Connecticut, with its own old-timey Flying Horse Carousel right in town. If you stay at the Watch Hill Inn, you’ll get privileges at the Ocean House, another iconic, historic hotel just down the street, with a full-service spa and restaurant. If you go, dress for crisp autumn walks on the beach, and plan to visit area attractions like Mystic Aquarium, local farms, nature centers and local shops and restaurants.
Woodstock, New York
You could do this in a day trip, but it’s more fun to stay at least one night, if you can. Most people associate Woodstock with peace, love and happiness, but don’t write this town off as a hippy-only stomping ground. Today, it’s home to a variety of artists who sell their wares in the two dozen or so shops along the main drag in the bustling downtown. My kids ate an entire vegan lunch — chickpea fries, included — at the cute-as-a-button downtown Garden Cafe, we walked along the creeks and waterfalls in town, and we spent a day walking/biking along the paved trails lining the grand Ashokan Reservoir. We’ve been planning a trip back just to go for another short stack at the Phoenicia Diner, a vintage roadside dinner with fabulous food in the middle of the mountains. We rented a cottage on AirBnB, and it was basic but really cute, not nearly as nice as this artist’s retreat available this weekend at $285 per night.