A Perfect Weekend in Cumberland Valley
Cumberland Valley’s art galleries, wineries, and artisan candy and chocolate shops make for a decadent weekend getaway with your special someone or a group of friends. We’ve created a sample itinerary with some of the best places to browse local art, sample PA wines, and try all the sweet treats unique to this region. If you time it right, you may even be able to take an art class or learn a new craft!
Day One
If it’s a lovely day for a drive, consider starting your weekend with the Covered Bridge & Wine Loop, which will guide you to three different wineries and eight historic covered bridges as you enjoy the gorgeous mountain scenery of southcentral Pennsylvania in nearby Perry County. (Please drive responsibly.)
If you’d rather start with art, explore the suggestions on the Cumberland Valley Artisan Adventure Trail to discover some of the cutest shops and galleries in the region featuring local artists and craftsmen.
When you’re ready for something sweet, stop by the Pennsylvania Bakery in Camp Hill for beautifully decorated cupcakes, pastries, cookies, cake pops, pies, and seasonal treats. Or visit SweeTreats Bakery in Lemoyne for a rotating selection of mouthwatering, made-from-scratch treats, including sugar-free and keto items. Read more about Cumberland Valley's best chocolate, candy, and dessert options.
If you visit from February to May, be sure to sign up for the Coffee and Chocolate Trail for more recommendations on where to go for delicious coffee and decadent desserts throughout your stay.
End your day by supporting local artists and purchasing something to remember your trip. Browse works of art, made-in-America gifts, and decor at the Valley’s local artisan shops like the Village Artisans Gallery (pictured above) in Boiling Springs and The Cumberland Shop in Shippensburg.
Day Two
Spend your second day in Carlisle, a historic town with so much to see and savor!
Take a class at the Carlisle Arts Learning Center or browse their galleries and exhibits featuring local artists. Shop fine art at The Garden Gallery, which has featured the work of locally and nationally recognized artists since 1976. Or stroll through The Trout Gallery on the campus of Dickinson College to enjoy a blend of fine arts from ancient artifacts through contemporary works, plus unique student exhibits featuring exciting young artists.
Spend your afternoon relaxing at the cozy Castlerigg Wine Shop. Enjoy a tasting or glass of wine from Seven Mountains Wine Cellars and take a bottle or two home to enjoy later. Owner Alan Tumblin can even suggest the best wine to go with any chocolates you plan to buy this weekend.
With so many excellent wineries nearby, there’s no need to limit yourself to just one! Visit Totem Pole Ranch & Winery (pictured above) on the outskirts of downtown Carlisle, which offers ten varieties of wine from grapes grown on their ranch. This disabled veteran-owned business has a tasting room with food available for purchase.
Just a 10-minute drive from downtown Carlisle, you’ll find The Winery at The Long Shot Farm. Here, you can relax on the deck with gorgeous views of the vineyard and mountains while savoring wine at the first winery in Cumberland Valley to grow, process, and bottle its own grapes.
Cumberland Valley is a chocolate paradise known for its unique chocolatiers and candy shops, many of which are located in Carlisle! Within a few short blocks, guests can savor the nostalgic joy and extensive candy selection at Georgie Lou’s Retro Candy, gourmet Swiss milk and dark chocolates at Mummert Chocolates, and imported and award-winning artisan chocolates at Exquisite Chocolates. Each shop will please your taste buds with its delicious and unique offerings.
Carlisle is also home to a Lindt Chocolate Factory Outlet store. Stop by and pick out your favorite truffle flavors from the large bins and discover varieties not available elsewhere.
Day Three
Start your last day of your Cumberland Valley getaway in Mechanicsburg, a charming town that lives up to its motto, “A Good Place to Live.”
Browse local artwork and take a class at the Art Center School & Galleries in Mechanicsburg, or visit Pure Galley to browse or shop for fine art and artisan gifts.
Stop for lunch at Luna Italian Cuisine, where you’ll find authentic Italian dishes and a carefully curated selection of cocktails and wines to enhance your dining experience.
Before you head home, visit Macris Chocolates (pictured above), where you can pick from over 100 varieties of chocolates to make the perfect box to commemorate your sweet weekend in southcentral Pennsylvania. Macris also has another location in Lemoyne.
As you can see, the Cumberland Valley is an excellent place to experience unique and memorable artwork, relax at a wine tasting or two, and savor sweet treats like chocolate, candy, and desserts. These recommendations have only scratched the surface! Discover more wineries, and sweet treats, and view additional ideas with our Art Lovers Getaway. Then check out our Food & Spirits page for recommendations for restaurants, breweries, and more to enjoy during your visit.
