I spent the weekend in New Haven, Connecticut, for my nephew’s wedding and it turned out to be the perfect New England fall getaway. Between historic sights, incredible food, and quality family time, it was one of those weekends that just fills your cup.

(You can listen to my podcast episode about the trip below! You won’t believe the travel blunder I made! Sheesh!)

Where We Stayed: The New Haven Hotel

We stayed at the New Haven Hotel, which turned out to be a great choice for location and convenience. Parking was easy (which isn’t always the case in college towns), and we were within walking distance of restaurants, coffee shops, and the Yale campus.

The rooms were nice, nothing over the top but clean and comfortable. Prices were definitely higher than usual because it happened to be Yale Alumni Weekend, so the town was buzzing with activity.

Even with the busy weekend schedule, I still made time to get in two FASTer Way workouts at the hotel gym. I did an upper body day and a leg day. The beauty of these workouts is you can do them anywhere and they only take 30 minutes. These keep me energized and stay consistent with the habits that make me feel my best. The gym was small but had everything I needed, and it felt so good to keep moving while traveling.

A hotel gym is my favorite way to feel great while traveling!

Thursday: Pizza and Family Time

We flew in Thursday afternoon and went straight to Frank Pepe Pizzeria Napoletana, known as the original New Haven style pizza spot. Their thin, slightly charred crust with that perfect balance of chew and crisp was so good.

New Haven is actually known as the pizza capital of the country, and after trying Pepe’s, I get it. The competition here is serious, with other famous spots like Sally’s Apizza and Modern Apizza drawing lines around the block.

That night we met up with family and the wedding party for drinks after the rehearsal dinner. It was the start of a full weekend of celebrating.

Friday Morning: Yale Strolls and Local Eats

We grabbed coffee at Claire’s Corner Copia, a cozy, vegetarian-friendly café right near Yale. It’s one of those local staples where students and alumni seem to gather year after year.

A power walk through Yale’s campus was a great way to start our day.

From there, we walked around Yale University, and wow, the campus is stunning. Think Gothic-style buildings, intricate stone carvings, and tree-lined courtyards that look straight out of a movie. Don’t miss:

Old Campus, the heart of Yale’s history
Sterling Memorial Library, which feels more like a cathedral than a library
Harkness Tower, which chimes every 15 minutes and adds to the fairytale feel of campus

We had breakfast at Patricia’s Restaurant, a true hidden gem. The food was excellent with big, hearty portions and perfectly cooked eggs, though the vibe is more small-town diner than trendy brunch spot.

A bacon and tomato omelet with potatoes is my go-to order for breakfast!

The wedding ceremony was at St. Mary’s Church in downtown New Haven. The church itself is gorgeous, with stunning stained glass and high vaulted ceilings that gave it such a timeless feel.

The reception was held at the New Haven Lawn Club, and it could not have been more beautiful. The space had that perfect mix of old-world charm and modern elegance, with high ceilings and chandeliers. The bride’s family went all out! The food was amazing and the dance floor stayed packed all night.

Saturday: The Coolest Brunch Idea and Exploring the Coast

The bride’s family hosted a brunch at their home the next morning, and I have to say it was one of the most creative brunch setups I’ve ever seen. They had a breakfast food truck parked in the driveway where you could order a breakfast bowl, sandwich, or burrito.

Inside, there was a full coffee bar set up on the kitchen island, plus fruit, donuts, and plenty of room to mingle. It was casual, creative, and such a great way to keep the celebration going. I’m definitely stealing this idea for future family gatherings.

After brunch, we decided to make the most of the fall weather and took a drive to Mystic, about an hour from New Haven. It’s an adorable coastal town known for its harbor views, charming shops, and of course, Mystic Pizza (yes, that Mystic Pizza from the movie). We couldn’t resist grabbing a slice!

We also stopped at a nearby pumpkin patch for some quintessential fall photos before driving over to Essex, another postcard-perfect New England town. Essex has that small-town charm with historic homes, boutique shops, and views of the Connecticut River that are absolutely beautiful this time of year.

Back in New Haven, we had dinner at Noa, a fantastic Thai restaurant just a short walk from our hotel. The flavors were fresh, the presentation was gorgeous, and it was one of the best meals of the weekend.

We ended the night back at my sister’s Airbnb, watching the Notre Dame football game with family. It was such a relaxed, cozy way to wrap up a whirlwind weekend.

Sunday: Sendoff

Before heading to the airport, we squeezed in breakfast at The Pantry, another local favorite. I can see why. It was absolutely delicious. Think homemade pancakes, fresh-brewed coffee, and that classic diner energy that just feels like comfort.

As we drove to the airport, the trees were bursting with color, reds, oranges, and golds glowing in the morning sun. It was the perfect ending to a perfect fall weekend in New England.

Final Thoughts

Between the pizza, the people, and the picture-perfect scenery, New Haven totally surprised me. It’s more than just a college town. It’s a mix of history, energy, and that cozy New England charm that makes you want to come back.

If you’re looking for an easy fall weekend trip packed with great food, beautiful sights, and a dose of nostalgia, add New Haven (and nearby Mystic and Essex) to your list.

A Fall Weekend in New Haven, Connecticut