The view of Harpers Ferry, WV from a nearby hike
A late fall road trip from the New York area to Harpers Ferry, WV mixes history, nature, small town charm, and kosher food stops along a convenient route… and that’s exactly what we did a few years ago over the short holiday weekend.
Traveling over Thanksgiving weekend, this itinerary follows a loop south through Lakewood and Baltimore, continues to Harpers Ferry for Shabbat at a cabin in the woods, and returns north through Philadelphia before heading back home.
This is an actual itinerary I completed with my family on a recent Thanksgiving weekend. If you have a family, this trip is ideal as long as everyone can hike and take long walks.
Kosher Stops and Driving Toward Maryland
Leaving Wednesday (or Thursday!) afternoon, Lakewood makes a slightly out-of-the-way stop for dinner before continuing south. The large kosher scene there offers multiple family-friendly dining options to enjoy before getting back on the road.
On our travels, we enjoyed Lamppost Bistro in Tom’s River, an excellent steakhouse that also served as a Thanksgiving dinner for us on our travels. Lakewood has many high-end kosher restaurants and steakhouses worthy of a detour, especially for a big meal on Thanksgiving with the family just before a long drive.
Continue driving toward Baltimore and stay overnight nearby. Baltimore offers both kosher grocery options and restaurants, making it easy to pick up food for the weekend and enjoy a relaxed breakfast or lunch before moving on.
Stocking Up on Kosher Food in Baltimore
Because it was Friday morning, we grabbed breakfast with local friends at Croustille Cafe, a cute bakery / cafe with excellent pastries and a great place to grab challah (or even sufganiyot- if in season).
Baltimore also has fantastic kosher supermarkets, like Market Maven and Seven Mile Market, that have freshly prepared Shabbos food, fresh sushi, and any other foods or items you’d need to prepare your own Shabbat at a cabin in the woods.
Exploring Baltimore and Continuing West
If you end up in town on Thursday instead of Friday, explore Baltimore’s parks and harborfront, which are great for a relaxed family stroll. After stretching legs and taking in the waterfront views, there are a number of great museums that are great for families in the area. My favorite is the American Visionary Art Museum, which is fun for both adults and children alike.
Afterwards, continue west toward Harpers Ferry. The 1 hour drive becomes more rural as highways give way to winding roads and wooded scenery, signaling the shift into slower small town territory.
Shabbat in Nature in Harpers Ferry
Harpers Ferry does not have any Jewish life, so plan accordingly for Shabbat. This destination is all about nature and quiet. Staying in an Airbnb overlooking the river and surrounded by woods made for a peaceful and memorable experience, especially in late fall when the air is crisp and the leaves are thinning. With no community infrastructure, this Shabbat is truly unplugged, offering time to relax, read, spend time together, and enjoy the outdoors.
Hiking Above the Rivers
One of the highlights of Harpers Ferry is the hike that begins right from town. On Sunday, head to the town and start near the historic district, near the old (and still active!) Amtrak station, and take the pedestrian bridge over the river into Maryland. From there the trail heads uphill through a wooded path, climbing for about an hour before reaching dramatic views overlooking Harpers Ferry and the point where the Potomac and Shenandoah rivers meet. This is a rewarding family hike with panoramic scenery and a true sense of accomplishment once you reach the overlook. [If you’re looking for this hike on Maryland Heights via Harper’s Ferry on AllTrails, it’s called the Maryland Heights via Harper’s Ferry].
Enjoying Harpers Ferry Town
The town itself has historic streets, preserved buildings, river views, and a calm atmosphere. It feels tucked away from time, offering an easy pace and opportunities to explore without crowds. Even with colder weather, walking around town and taking in the water views adds to the charm of the trip.
Returning North and Philadelphia Stop
Leave Harpers Ferry Sunday morning and drive toward Philadelphia. Fall and winter in Philadelphia often bring weekend markets, outdoor craft and holiday fairs, and seasonal pop ups that are fun to explore. The city also has excellent museums to choose from, including both family friendly and art focused options. Philadelphia’s kosher restaurants make it a convenient place to stop for lunch or an early dinner before continuing back to New York.
To map out kosher restaurants near you or wherever you’re traveling, make sure to download our free kosher restaurant app here for all iPhone and Android devices.
This trip combines outdoor adventure, peaceful Shabbat time in nature, family-friendly stops, and kosher convenience along the route. Harpers Ferry in particular delivers a mix of national park-level scenery and historic character, making it an ideal Thanksgiving weekend escape from city life.