My 5 Fave October Day Trips Close To Jersey

Happy October, spooky friends! I love a good road trip and especially a day trip where you can hit some great spots and still make it home in the same day. Below are some ideas for Fall adventures as you begin to figure out which weekends you have some free time. These are some of my favorite places to go to enjoy crisp, chilly weather and charming small town autumnal vibes. For travel time reference, I’m in Union County:

Woodstock/Kingston, NY

I will preface this by letting you know that Woodstock, NY was not the site of the famous music festival. However, Woodstock keeps the spirit of peace and love alive in this small town in Ulster County, NY. There are great outdoor activities here like hiking or simply taking in the beautiful views. But Woodstock itself is home to some great shops and dining along Tinker Street. Visit Bread Alone for incredible fresh breads or to grab breakfast or lunch. Candlestock is a candle lover’s dream with everything from classic candles to funky ones (like a mini eyeball candle, perfect for Halloween) and a massive piece of candle drip artwork. Step into Garden Cafe for a vegan meal or go to Tinker Taco Lab for tacos and cocktails. Art is always important so round out your day with a visit to Woodstock Artists Association and Museum or head to one of my personal favorites, Tibetan Arts and Crafts

About 20 minutes from Woodstock is Kingston, NY, another quaint town and where I started this day trip when I went in 2019. There is also a Bread Alone location (technically in Lake Katrine) Here’s how my day trip went:

Drive Time: My house to Kingston is 1 hour 52 mins or direct to Woodstock is 2 hours


Jim Torpe, PA

Note: These were the 2019 dates

I went to Jim Thorpe in early October 2019 for my bestie’s bachelorette weekend and October really is prime time there. You get to experience the Fall magic as well as some Halloween vibes. Jim Thorpe is picturesque with a foliage train ride, a lovely downtown, and plenty of opportunities for shopping and eating. A must see for any Harry Potter fan is Muggles’ Mug, the best little wizarding world of coffee. You can get a Butterbeer latte (butterscotch and caramel) or the seasonal fave of Pumpkin Juice (yes, a pumpkin spice latte). Horizons is a whole vibe and will make you feel like you’re somewhere inside of Jerry Garcia’s mind and then you can swing by the Mauch Chunk 5 & 10. When you get hungry, I recommend Marion Hose Bar for a menu with plenty of options and some nice cocktail, beer, and wine selections. Another great option (that also has breakfast) that I wanted to stop into but never had the chance, is Broadway Grille & Underground. For my friends with a spiritual or witchy side, I also recommend Gem Thorpe (I know, such a cute name) and The High Priestess. If you like a nice winery stop, grab a glass at Big Creek Vineyard. After your strolling time is done, take a ride on the Lehigh Gorge Scenic Railway for relaxing train ride and views of the foliage. Jim Thorpe is located in the Poconos so it’s very easy to make it a long day trip or turn it into a weekend getaway. They also have plenty of events so check out https://www.poconomountains.com/jim-thorpe/ for the info!

Drive Time: My house to Jim Thorpe is 2 hours


Amish Country (Lancaster County, PA)

I have been going to Amish County in Lancaster County, PA pretty much since I was born. You can squeeze a lot of eating into a day trip if you really put your mind to it. Fair warning, many options are closed on Sundays so plan this one for a Friday or Saturday. Head out early and grab a breakfast buffet at Yoder’s where you get plenty of options for $9.99 on a weekday and $10.99 on a Saturday. Once you’re nice and full, get some walking in with shopping on a visit to Kitchen Kettle Village where you can buy items like jams, cheeses, olive oils, and candles. You can have a wine tasting at Waltz Vineyards and/or a coffee at The Roasted Rooster. There’s also a lovely store called The Country Life that has all of those little country home decor items and furniture that make you want to abandon city life and move to the farmlands. After Kitchen Kettle, you may want a lil’ nosh so swing by Kauffman’s where they make fresh cider donuts right out front. I can confirm that they are wonderful with just the right amount of sugar gracing the outside. Inside of Kauffman’s there’s an array of produce including almost every variety of apple you can think of. The Bird-In-Hand Farmers Market has been a staple in all 35 years of my life. My family and I always stop here and usually grab a hot dog at one of the counters, get some meats and cheeses to take home, sip on a 25 cent cup of apple cider, and buy some baked goods. But my baked goods tip is to make the extra trek and visit the Bird-In-Hand Bakeshop where my favorite chocolate shoofly pie is made and there’s a little petting zoo with goats. Your final stop, should your stomach be able to handle it, is Shady Maple Smorgasbord. I need you to understand that this buffet is 200 feet long and that you will be more full than you ever thought you could be. They also have a market next door where you can get some incredible deals on produce, meats, and prepared foods. TL;DR: lots of food, bring a cooler to take things home, goats!, wear pants with a little give. 

Since many of these require a bit of driving, here are the addresses:

  • Yoders: 14 S Tower Road, New Holland, PA

  • Kitchen Kettle Village: 3529 Old Philadelphia Pike, Intercourse, PA

  • Kauffman’s: 3092 Old Philadelphia, Bird-In-Hand, PA

  • Bird-In-Hand Bakeshop: 545 Gibbons Road, Bird-In-Hand, PA

  • Shady Maple: 129 Toddy Drive, East Earl, PA

If you find yourself with extra time and/or want more options, here are some other faves:

  • Rumspringa Brewery: 3174 Old Philadelphia Pike, Bird-In-Hand, PA

  • Thistlefinch Distillery: 417 West Grand Street, Lancaster, PA

  • Julius Sturgis Pretzel Bakery: 219 E Main Street, Lititz, PA

  • Wilbur Chocolate Factory: 45 N Broad Street, Lititz, PA

Drive time: my house to Yoder’s is just over 2 hours


Sleepy Hollow, NY

I love all things spooky and if you do as well then a trip to Sleepy Hollow should be on your list. Start off in Tarrytown where you can visit places like Coffee Lab Roasters Inc. and The Cherry Door Thrift Shop. You can then head to the Scenic Hudson RiverWalk Park to enjoy the views. Then it’s off to Sleepy Hollow to hit the best places such as Sleepy Hollow Cemetery (where you can see Washington Irving’s gravesite), Old Dutch Reformed Church, Headless Horseman Bridge, and the Headless Horseman Statue. If you have time, plan a visit to Kykuit, a Rockefeller estate built in the early 1900s. Fall is also a great time for a stop at Captain Lawrence Brewing Company where there is plenty of outdoor seating, great beer, and yummy food (I loved the shishito peppers). From there, if you’re lucky enough to snag a ticket, you can enjoy the nighttime fun of The Great Jack O’Lantern Blaze in Croton-On-Hudson. This experience brings you thousands of hand-carved jack o’lanterns with fun features like the Headless Horseman Bridge, giant creatures like dragons and spiders, and the Statue of Liberty. And really, what’s more October than strolling through a cemetery, doing Headless Horseman things, and then seeing a bunch of beautifully carved pumpkins? 

Drive Time: my house to Tarrytown is just under 1 hour

Rhinebeck & Red Hook, NY

Truth be told, my sole purpose for wanting to go to Rhinebeck centered around Samuel’s Sweet Shop. This tiny shop has been around for nearly 30 years and Paul Rudd and Jeffrey Dean Morgan helped save this place when its future was uncertain. You can find old school candy, wonderful homemade chocolates, and great coffee. I absolutely loved visiting and plan to return. Also in Rhinebeck is Oblong Books (recommended to me by my friend Loren!) and I love a nice independent bookstore. I also got to stop into The Kroeg which had solid beers and a very cool atmosphere. Rhinebeck had some nice dining options I unfortunately did not get to visit like Bread Alone (yes, another!), Cinnamon Indian Cuisine, and Terrapin. However, I didn’t spend my whole day in Rhinebeck and here is a breakdown of the day:

  • Breakfast at Historic Village Diner in Red Hook, NY 

  • A stop at Greig Farm in Red Hook for cider doughnuts and to visit some goats

  • Rose Hill Farm in Red Hook for more cider donuts (they also have apple picking and a taproom!)

  • Tousey Winery in Germantown for a flight of local wine

  • From The Ground Brewery in Red Hook for beer in a mason jar

  • Rhinebeck for a few stops and wandering around town

  • Plan Bee Farm Brewery in Poughkeepsie where I had a very tasty Barn Beer with coriander

  • Benmarl Winery in PoughkeepsieI know this was on an earlier list but it’s truly one of my favorite wineries and also can work with this day trip

Drive Time: My house to the Historic Village Diner is just under 2 hours or right to Rhinebeck is also just under 2 hours


I based most of these recommendations on places I’ve personally been to. I like to provide you with info on day trips and locations I have actually visited/researched. If I missed any of your favorite spots in these towns, please shoot me a message so I can check them out on my next trip. I hope you enjoy your Fall road trips! Be sure to tag me if you check out any of these spots, I love seeing how you experience my recommendations. And again, Happy October!

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