Escape NYC With These 5 Easy Fall Roadtrips

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There are few things I love more than autumn in the Northeast. I love the warm colors of flora and fauna that develop. Celebrating harvest, wearing cozy sweaters, and enjoying the best flavors of warm drinks and baked goods are some hallmarks of the season.

Living in NYC offers plenty of opportunity for fun during any season, but sometimes it is great to just escape for a little while. Luckily there are plenty of places that are a short commute from the city that will allow you to bask in the brilliance of fall.

1. North Fork, Long Island

City dwellers often jump to the conclusion that the Hampton’s is the only place to be on Long Island, but the quieter hamlets on North Fork offer the ideal setting for getting away from it all. Dozens of farms and wineries make it a fantastic fall destination.

Stay Here:

Bed & Breakfasts are a great option in this area, especially if you’re planning a romantic weekend. Check out Quintessentials Bed & Breakfast, which has fresh farm-to-table cuisine and a full-service spa. For a higher price tag, they offer the “full experience” package of spa services, wine tastings, and dinner.

Bed & Breakfast’s not for you? The Gallery Hotel is an intimate and quirky boutique hotel with an onsite cafe and gallery. This centrally located inn only has ten rooms, so make sure you book in advance.

Eat Here:

If it’s good, old-fashion Long Island seafood you’re looking for, then head straight to Southold Fish Market. You will enjoy some of the freshest seafood on Long Island in a welcoming atmosphere that will make you feel like part of the family.

For farm-to-table fine dining, we highly recommend the North Fork Table. They will happily let you know where your food is locally sourced from and offer spot-on wine pairings with your meal.

Things to Do:

No trip to North Fork would be complete without a few winery tours. Long Island Wine Country lists over 30 wineries. To make your adult tasting journey even better there is now complimentary trolley service on the wine trail through November 11th. If you prefer cider or beer, head to Woodside Orchards or Greenport Harbor Brewing Co.

While there are dozens of farms in North Fork, Harbes Farm is one of the most famous – and for a good reason. There are vineyards, apple orchards, pumpkin patches, concessions, and activities for the kids. During the fall, they even have a family friendly haunted corn maze at night.

No matter what village you end up in, keep your eyes peeled for bustling farmer’s markets and endless antique shops.


2. New Paltz, NY

If you are looking to connect with nature this fall, then New Paltz is the place for you. While there are plenty of great things to do in this city, it’s best features, by far, are its natural assets.

Stay Here:

Mohonk Mountain House is THE place to stay in New Paltz. This gorgeous mountaintop resort boasts an award-winning spa and top-notch farm-to-table dining. With on-site stables, golf courses, and outdoor adventure excursions you may not want to leave the resort.

Eat Here:

If you do decide to leave the Mohonk Mountain House, you will want to check out A Tavola Trattoria. This excellent dining restaurant is serving up rustic Italian fare with locally sourced ingredients. If a casual dining experience is more your speed, head to P&G’s for some classic pub fare favorites.

Things to Do:

Hiking the Mohonk Preserve is a must when in New Paltz. Though possibly exhausted in the end being surrounded by nature and rewarded with breathtaking views will make it all worthwhile. Nearby Twin Orchard Farms is a must for anyone looking to sip cider and pick apples.

If it’s historical adventure you seek, Huguenot Street has you covered. This living history museum features a tour through the lives of early New Paltz settlers, refugees from France. For something more seasonal, visit on a Friday or Saturday evening after October 13 for the Haunted Huguenot Street tour.

3. Warwick Valley, NY

Warwick is a lesser known destination that should be at the top of the list for anyone who enjoys relaxation. With dozens of farms and orchards, fall is a perfect time to visit this area. Warwick Valley Township is home to 3 villages – Warwick, Greenwood Lake, & Florida, each contributing to Warwick Valley’s flair.

Stay Here:

Orange County’s hidden gem has very few actual hotels, so inns and bed & breakfasts are the way to go if you plan on staying a night or two in this charming area. Check out Ashford Cottage, a warm and pleasant B&B, where you will feel like a part of the family. Another great option is Warwick Valley B&B, with it’s cheerfully themed rooms and hearty breakfast spread.  If comfortable accommodations and delicious breakfast aren’t enough to draw you, both inns are also within walking distance of the towns best highlights.

Eat Here:

If you are looking for a high-end exceptional dining experience, head to Chateau Hathorn. Situated in a restored historic homestead, you will enjoy a gourmet meal with heavy European influences. If you prefer good beer and quality food in a comfortable, low-key setting, then check out Yesterday’s Irish Pub. They’re serving up fan favorites with a touch of Irish hospitality. No matter where you decide to eat, be sure to stop at Bellvale Farms Creamery for an unbeatable sweet treat.

Things to Do:

Warwick Valley’s location makes it ideal for farming, and therefore it is home to a multitude of apple orchards. For classic fall activities head out on the Warwick Valley Apple Trail and see how many farms you can visit. Apple Dave’s (formerly Applewood) & Warwick Valley orchards are both also wineries, so if you are looking for adult-oriented fall fun, those should be at the top of your list.

We highly recommend taking in a movie while you’re in Warwick because you are guaranteed a double feature in a cozy setting at the Warwick Drive-in. Head over to Main St. for some fantastic antiquing and specialty shops, you’re bound to find a few hidden treasures. Before you leave, make sure you stop by the nearby Sugarloaf Art & Craft Village and support some fantastic local artisans.

4. Saratoga Springs, NY

This capital region city has been a vacation haven for centuries, drawing visitors wishing to soak in the spring’s medicinal spas. Aside from spa aficionados, foodies, history buffs, nature lovers, and gamblers will all love Saratoga Springs.

Stay Here:

Centrally located is Saratoga Arms, an elegant, family-owned hotel. Hotel staff is on standby to assist you to craft the perfect trip, taking all the stress out of planning. Guests of the hotel also receive a complimentary, locally sourced, gourmet breakfast. The Gideon Putnam offers an elegant stay at a reasonable price. The hotel borrows its name from the city’s founder and has a rich history of its own. The hotel boasts a full-service spa, on-site restaurant, luxurious accommodations, and shuttle service to the nearby casino.

Eat Here:

Sperry’s Restaurant is a must for fine dining. Serving a variety of dinner staples and creative menu items in their historic location since 1932, it is a popular destination for visitors & locals alike. For casual comfort food head to Comfort Kitchen located in the Saratoga Marketplace. They are serving all locally sourced, seasonal comfort item and have something on the menu to please even the pickiest eaters.

Things to Do:

No trip to Saratoga is complete without a tour of the famous Saratoga Race Course. There are no horse races taking place in the fall, but tours of the historical course run throughout the offseason. Take in the beautiful fall foliage with a hike through Saratoga Spa State Park, pack a picnic or play a game of golf while you’re there.

Saratoga is renown for its numerous mineral springs. These “healing waters” have been drawing crowds for centuries. Be sure to carve out some self-care time in one of the many spas like Roosevelt Baths & Spa. Saratoga is also home to many museums, such as New York State Military Museum, The Saratoga Automobile Museum, and National Museum of Racing and Hall of Fame.

5. Sleepy Hollow, NY

History buffs and Halloween addicts alike will love all this village has to offer. There is no better time to visit Sleepy Hollow then in fall when the already lively town brings their history to life. The town itself has become synonymous with haunts thanks to Washington Irving’s tale of the Headless Horseman. A weekend in Sleepy Hollow is bound to appeal to all you love about autumn.

Stay Here:

Castle Hotel & Spa is located in the adjoining village of Tarrytown and boasts a rich gilded age history. This sprawling estate features an Asian inspired spa, as well as a gourmet restaurant.

Check out Tarrytown House Estate for something a bit less opulent but equally rich in history. Be sure to check out their on-site restaurant, Cellar 49 (reservations recommended)

Eat Here:

Go casual at the Bridge View Tavern, where you can sip craft beer, or Lefteris Gyro, which is family friendly and offers a delicious selection. If you are looking for something fancier, look no further than The Twisted Oak, which serves up Italian influenced American fare with a farm-to-table fresh taste.

Things to Do:

There is no shortage of fun in Sleepy Hollow or nearby Tarrytown. Start your day by checking out the local Farmer’s Market, which takes place every Saturday until Thanksgiving and has a vast array of fresh produce, locally baked goods, and even some NYS wines. If history is your thing, we recommend checking out the historic Lyndhurst Castle, fully decorated for Halloween through October. They’re closed on Tuesday & Wednesday, so plan your visit accordingly. The Rockefeller Estate of Kykuit will also provide you with a rich history lesson, as well as spectacular gardens, an underground art gallery, and a sizeable collection of classic vehicles.

Philipsburg Manor allows you to enter the year 1750, when the manor’s milling, trading, and agriculture were part of a vast enterprise. If you prefer haunts to history, be sure to plan your visit to Philipsburg after sundown when the ghosts rise to tell their tale. Every weekend in October sees this quaint museum transform into Horseman’s Hollow, a town driven mad by the Horseman, himself.

Sure to leave you with chills are the haunted tours, led at night by lantern, through the Sleepy Hollow Cemetery. They offer themes such as, “Mayhem & Murder” or “The Good, The Bad, and The Unusual.” For those faint of heart, less spooky tours are offered in daylight, which highlights some famous names found on the grave markers around the cemetery. Finally, not as mysterious as it is spectacular, is the Great Jack o’ Lantern Blaze at Van Cortlandt Manor. Meander through the grounds and take in the view of more than 7,000 hands sculpted Jack o’ Lanterns, some in ways you have never seen before. Tickets for this must be purchased in advance and often sell-out, so be sure to plan accordingly.

Do you have a favorite NY getaway destination that isn’t listed here? Be sure to let us know about it!

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3 thoughts on “Escape NYC With These 5 Easy Fall Roadtrips

  1. Great post! I love the Castle Hotel! I will have to add it to my to-do’s! I have been to Saratoga for a conference – I loved it. The main road was pedestrian friendly, great shops and tons of places to eat outside at restaurants or in. They also have an excellent local coffee shop – I wish I could remember the name!

    1. Thank you so much for stopping by! Castle Hotel is awesome, I actually have an overnight booked there in January for my friend’s birthday. A nice spa day and evening of good food and wine – I can’t wait. I have family in Saratoga, so we love going up there for mini trips. They have two great coffee shops that I love visiting. One is Uncommon Grounds & the other is Saratoga Coffee Traders. They’re on my must list for morning coffee while I am in town. There really is so much to do there, though.

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