Pennsylvania's Rural Borough Between Hershey And Baltimore Brims With Wine, Orchards, And Small-Town Charm

A drive between the big-city attractions of Baltimore and the popular spots in Hershey takes you through the agricultural expanses of southern Pennsylvania. Right in the middle of that trip, you can find a rural borough north of the Maryland line. This is Stewartstown, a community in York County where there's a plethora of farmland and a preserved downtown area. You can see its history in the well-kept buildings along Main Street, which follows a segment of a colonial-era wagon road that once connected York, Pennsylvania, with Baltimore.

A central piece of this history that you can experience is the Stewartstown Railroad. It is one of the oldest continuously operating short-line railroads in the United States, and it continues to operate passenger excursions. For more railway adventure, about 21 minutes away in Pennsylvania's charming borough of Seven Valleys is the perfect getaway for peaceful railbiking and scenic fall foliage. Another great aspect of Stewartstown is the prominence of its wineries and orchards. These have become destinations where you can go for tastings or spend an afternoon picking seasonal fruit.

Your visit might line up with the community life, which includes events like an annual Eureka Volunteer Fireman's Carnival held in the summer and a fall festival organized by the local Lions Club. If you are looking for local recreation, Hopewell Area Recreation & Parks runs a complex with a quaint trail, a playground, and sports fields. The borough's quiet setting and its proximity to the highway (Interstate 83) have made it a nice residential area for people who commute to jobs in the larger hubs. If you're flying in to visit Stewartstown, the most accessible major airport for your travel is Baltimore/Washington International Thurgood Marshall Airport (BWI), which is about a 55-mile drive.

Stewartstown also has several vineyards where you can spend an afternoon sipping some reds and whites. Allegro Winery is open daily with a large list of wine varieties and a tasting room for smaller groups. You can buy wine to drink on-site, and the winery sells cheese and charcuterie boards to go with tastings. From May through September, your visit can line up with the winery's outdoor music series on weekends. Another local producer to check out is Balla Cloiche Vineyards, which is only for the adults in the crew to keep up a quieter vibe. It produces small-batch, estate-grown dry wines, and the tasting room is open on weekends. There's live music on the docket for most Saturdays, too.

Naylor Wine Cellars is another area staple with its own large lineup of products and a separate tasting room for you to sip in. You will also find Pinnacle Ridge Winery, a producer that has received many awards in Pennsylvania, which, over the years, moved its winemaking operations to Stewartstown. A tasting room on-site gives you an introduction to its wine portfolio, which includes a few different standard varieties. The Aviator Brew Hub, a brewery and restaurant in town, serves up a selection of wine on its self-pour tap wall. When you are visiting the area, you should consider using a ride-share app, as hotels are typically found in nearby towns. About 9 miles from Allegro Winery, you can check into the Red Lion Bed & Breakfast, or the Jackson House Bed & Breakfast is around 6.5 miles away in the town of Railroad. To keep the wine flowing on another leg of the trip, the town of Frederick has a tasty wine trail that weaves through gorgeous rural vineyards and Civil War sites about 1.5 hours outside of Stewartstown.

Orchards are another significant part of the area's draw. Shaw Orchards, a family farm that started in the early 1900s, is right on the Mason-Dixon Line. Similar to the Amish country gem called The Markets of Shrewsbury, the farm operates a market where you can buy fresh produce, jams, and jellies, and it also runs a pick-your-own program that lets you harvest your own fruit. Depending on when you head to town, you can pick strawberries, cherries, and blueberries. Raspberries have a tad longer picking season from June through September, after which your visit will be all about apple and pumpkin picking. Don't be surprised if you're invited on an autumn hayride, either, as these typically run on the weekends.

The cider scene is also developing in the area, like at Wyndridge Farm, which is about 11 miles away in the nearby town of Dallastown. It's a large spot on a 77-acre farm and has a cidery, a brewery, and a restaurant. You can go there to try its own line of craft ciders (like its original, cranberry, or pineapple mango ciders) and beers. It also has a seasonal beer garden, as well as an inn if you want to stay on-site. Back in Stewartstown, the Aviator Brew Hub makes its own Wing Walker Hard Cider, which you will find available on its self-pour tap wall similarly to the wine option. The Stewartstown Smokehouse & Beer Barn is a nice restaurant option that serves desserts like an Apple Pie Eggroll, which often uses seasonal ingredients like some of the local apples in the fall.