A Spring Weekend in Hershey & Gettysburg: Family, History, and Jai’s Birthday - May 2025

Our mid-May getaway to Hershey and Gettysburg allowed us to weave together family, friendship, history, and celebration — a spring adventure filled with good food, shared stories, historic exploration, and a warm celebration of Jai’s birthday.

⭐ Friday, May 16 — Arrival in Hershey & Dinner With the Kids

We left Canandaigua around noon, enjoying the long scenic drive through rolling farmland before arriving at the Londonderry Inn & Estate around 4 PM. The inn — a luxurious Victorian property dating back to the early 1840s — was even more beautiful in person. With its ornate trim, tall windows, and peaceful grounds shaded by mature trees, the estate felt like a gracious step back in time.

Our home for the weekend was the charming Carriage House, perfect for a relaxed family gathering.

That evening, we met Trace and Shayna for a casual dinner at The Chocolatier inside Hersheypark. The atmosphere was fun and lively — a perfect, low-key start to the weekend and a great chance to catch up with the kids in a sweet, Hershey-themed setting.

⭐ Saturday Morning — Downtown Hershey & Gettysburg Adventure

Saturday morning began with exploring downtown Hershey, enjoying its shops, walkable streets, and cheerful spring vibe.

Then we decided to take a spontaneous day trip to Gettysburg — one of the most historically powerful places in the country. We spent time browsing the downtown shops and then drove through the Gettysburg Battlefield, taking in the vast, rolling fields, monuments, and quiet reverence of the landscape. It was moving, haunting, and beautiful — one of those places that stays with you long after you leave.

⭐ Saturday Night — A Birthday Feast for Jai

One of the main reasons for this trip was to celebrate Jai’s birthday, and Saturday night became the heart of the weekend.

We gathered at the Carriage House with friends and family: Maddie, Peter, Lauren, Steve, Shayna, Trace, and Jai.

Instead of going out, we ordered take-out Indian food — warm, fragrant, comforting — and shared it around the table in the cozy Carriage House. The atmosphere was relaxed and joyful, full of laughter, cross-talk, stories, and that easy flow that happens among lifelong friends.

⭐ Sunday — Gourmet Breakfast & Farewell

On Sunday morning, we enjoyed a beautiful gourmet multi-course breakfast at the Londonderry Inn, full of fresh ingredients and thoughtful details. Between the historic setting, the gracious service, and the quiet countryside outside the windows, breakfast felt like the perfect close to the weekend.

We checked out mid morning and headed home to Canandaigua — tired, content, and grateful for such a rich, connection-filled getaway.

⭐ Reflections

This weekend was a perfect blend of time with the kids, reconnecting with friends, exploring Hershey and historic Gettysburg, relaxing at a beautiful inn, and celebrating Jai’s birthday in a warm, meaningful way.

It wasn’t a high-adrenaline adventure — it was something softer and deeper: a reminder of how special it is to show up for the people we love and make space for shared memories.