Your Perfect 4-Day Itinerary in Hershey PA

Get ready for your perfect 4-day itinerary in Hershey, PA, from check-in to check-out. With so much to see, four days is the best amount of time to settle in, unwind, and fully immerse yourself in all of the wonderful experiences Hershey has to offer.

Where to Stay

For the ultimate getaway experience, book your dream room at The Inn at Westwynd Farm, an enchanting bed and breakfast located on our picturesque farm estate just a hop and a skip from Hershey, PA. With 12 unique rooms to choose from and luxurious amenities such as fireplaces, jetted spa tubs, and private balconies, you will easily find your perfect accommodations. Whether you’re treating yourself to a long weekend to decompress, spoiling your loved one with a romantic Valentine’s getaway, or bringing the whole family, your stay with us will be your ideal home base. Don’t forget to check out our Winter Romance package if you plan to stay 2-3 nights.

Day 1: Check-In

Put the pavement behind you and embark on your journey to Hummelstown. You’ll know you’ve made it to the town center when you notice the brick-laden sidewalks and colorfully painted awning above the family-owned Hummelston flower shop. Venturing out into the woodlands, you can’t miss our proud estate surrounded by our horses grazing and ready to greet you.


Once inside, you’ll be delighted to find your room is ready and waiting for you to drop your bags. Eager to explore and hungry after your drive, you’ll make your way to Arooga’s Grill House and Sports Bar. With a vast menu (including vegan and gluten-free options) and a selection of craft beers, it’s the perfect way to wind down and settle into vacation mode. Spirits high, you’ll head over to the bustling town of Hershey to get your bearings and relish in your newfound sense of freedom.

wine flight tasting with various chocolate treats

Hopefully, you saved room for an early dessert because you’ve booked tickets to Hershey’s Chocolate World. There’s no way you can visit Hershey and not check this experience off of your bucket list! Between the HERSHEY’s Chocolate Tour, chocolate & wine pairing experiences, and riding the Hershey trolley, you’ll have a blast and learn about the history behind Hershey PA at the same time. If you time it right, you may even get to see the unveiling of the new chocolate sculpture. When your head hits the pillow tonight, you’re sure to dream of decadent chocolate.

Day 2

Wake up to the smell of coffee and step out onto your private balcony to soak in the picturesque view of equestrian farmland. Head down to the dining room overlooking the gardens to start your day with a wide selection of breakfast options, such as gingerbread muffins with cinnamon butter or ham and egg gratin. Give your favorite horse a nuzzle on your way out the door, and get excited for your first full day in Hershey, PA!

white roses by a roaring fireplace

Today is reserved for you and your special someone. Life gets busy, and this vacation is your hideaway where you can appreciate each other’s company without distractions. You know you deserve the best, so head to The Spa at The Hotel Hershey for the Couples Retreat Day Package. Between your couples massage, the buffet lunch for two at The Oasis (including tapas), and mani-pedis, you’ll reach a level of relaxation like no other. Not to mention you’ve booked the Enchanted Evening Package back at the Inn, so your relaxing day never has to end.

Waiting for you in your room is a beautiful rose bouquet, champagne, chocolate-covered strawberries, rose petals on your king-size bed, and a gift certificate to The Mill restaurant. When you return from your gourmet dinner, you relax by your fireplace and enjoy a special night alone together.

Day 3

Appreciating having so much free time, you stroll the grounds and take in the serene surroundings. Mist rolls through the pastures and friendly barn cats slink around. Eager to take in the natural beauty and explore some outdoor activities, you set out for a casual trek around Memorial Lake State Park. Along the way, you’ll appreciate the peaceful, scenic views of the lake.

white butterfly resting on hands

After lunch at Devon Seafood + Steak, you make your way to Hershey Gardens, a 23-acre botanical garden, and arboretum. Once inside, your senses are overtaken by the breathtaking beauty of the rare orchids on display as you walk amongst hundreds of butterflies in the Butterfly Atrium. As the butterflies gently land on you, it feels like time stops for a moment. To top the day off, you treat yourself to trinkets in the gift shop and a comedy performance at The GIANT Center. Good-hearted fun is the norm here in Hershey.

Day 4: Check-Out

Your last day with us is bittersweet, but you know you’re welcome back anytime! You spend your morning enjoying some retail therapy at the coveted boutiques downtown. Between Bella Sera Boutique, Brain Vessel, and Three Little Birds, you’re sure to find a souvenir that will remind you of the memories you’ve made over the course of your trip.


As you checkout from the Inn, you pocket one last sweet treat from the cookie jar. What is your idea of a perfect 4-day itinerary in Hershey, PA? Start with the basics and book your room today!


Published: February 2023