What To Do On A Weekend Trip From Philadelphia to New Haven, Connecticut

February 21, 2018
what to do in new haven

We wanted to plan a weekend trip from Philly, but realized that we had exhausted most of the options. Faced with a free weekend and no plans, Josh and I grabbed our laptops and started Googling, ‘best weekend trips from Philadelphia.’ Gettysburg; been there. NYC; visited way too many times. The New Jersey shore was overdone, and we’ve already explored Delaware. There were a ton of options, but we had done almost all of them before.

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Realizing that New Haven, Connecticut was only three hours from Philly by car, we quickly booked accommodation and went. We left on Saturday morning, got home by Sunday night, and had such a great time that we couldn’t believe we hadn’t visited New Haven before.


If you’re looking for a weekend getaway from Philadelphia, and you love, art, history, and culture, New Haven is an interesting place to visit. Here’s what to see and do there, as well as some options for where to stay.

What to do in New Haven, Connecticut


Frank Pepe Pizza

New Haven’s most famous pizza place was our first stop. After three hours of driving, we needed some fuel and the giant, square pizza was perfect. The pies here have been voted some of the best in the country, and from our experience, we could understand why. The crust is super thin and crispy, just how we like it. Try to get there by 11 am as lunchtime brings a long line. It’s nothing fancy, but the pizza is delicious.

Yale University Art Gallery

What to do in new haven

Photo: Tripadvisor

Free to the public, this art gallery spanned multiple levels and floors and was filled with artifacts, photography, European paintings, and modern works. The building itself is like a work of art. Spiral staircases lead you to new exhibits, and the intricate architecture, floor to ceiling windows, and peculiar sculptures make sure that there’s always something to see.

Wander Around The Yale Campus

what to do in new haven

The Yale Campus looks like something out of a Harry Potter movie. The architecture is stunning and the entire campus exudes sophistication. There are plenty of little buildings, shops, cemeteries, and gardens to pop into while you roam this famous, Ivy League school.

Yale Center For British Art

what to do in new haven

Separate from the Yale University Art Gallery, this building focuses on British collections. The paintings are drastically different from what you would find in a typical art gallery; full of bold colors and riveting scenes. It’s also free to the public, and if you’re lucky, you may stumble upon an interpretive dance performance while you’re there.

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The Owl Cigar Bar

what to do in new haven

Photo: The Owl Shop

This is one of the most unique New Haven bars that we found. In fact, I have never been to a bar like this before. It was dimly lit and had a 1920s, speakeasy vibe. While the bartenders were mixing up classic cocktails like Old Fashions and Moscow Mules, they were also selling a variety of cigars. The tables were full of regular guests, lighting up and watching the sports game. The walls were lined with glass cases of humidifiers, and the atmosphere was classy, yet casual. This seemed like the kind of place that hipster students and their down-to-earth professors may cross paths on the weekends.


what to do in new haven

Photo: Bar

Connected to a higher-end pizza restaurant, Bar is the place to go for craft beers and a game of pool. It’s a hotspot for the local college crowd and is usually packed on the weekends. In fact, they have a back room that opens up after 10pm and becomes more like a club than a restaurant. If you want to catch a DJ set and dance under a ceiling of color-changing lights, this is the place.

The Coffee Pedaler

what to do in new haven

Photo: Picssr

After an evening at Bar, you’ll need a little coffee pick-me-up the next day. The Coffee Pedaler is New Haven’s best cafe for coffee snobs. They have a nice pour over selection as well as a menu full of different coffee drinks. It’s a cute little space that is open, airy, full of light colors, and minimalistic decor.

The Pantry

what to do in new haven

Photo: Pinterest

This is one of the best breakfast places in New Haven. It’s across the street from The Coffee Pedaler so you can get food before caffeinating up. It’s a tiny place that serves up big flavors. Everything is handmade including the breakfast potatoes and French toast. The line tends to get pretty long so try and get there early. If you do have to wait, it’s totally worth it.

EBM Vintage Store

what to do in new haven

Photo: The Arts Paper

Looking for a vintage store in New Haven? This is your best bet. It’s bigger than it looks from the outside and is divided by decorated sections. Everything is neatly organized and there are vintage knick knacks alongside incredible furniture, home appliances, and clothes. You could get lost in here, so make sure you give yourself some time.

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Book Trader Cafe

what to do in new haven

Photo: The Shops At Yale

Part used book store, part cafe, this is a great spot for every book nerd. You can buy a new read, order a healthy lunch, and sit in the cafe to dive into both. The menu features items with names like, “Hamingway and Cheese,” “Schmear and Loathing in Lox Vegas,” and ” Memoirs of a Chicken.” Book nerds will love it.

Where to Stay in New Haven, Connecticut


Monks House

New Haven CT where to stay

Location: This vacation home is less than half a mile from many of New Haven’s top attractions such as:

  • Connecticut Children’s Museum
  • Audubon Arts District
  • City Hall
  • Center Church Crypt
  • New Haven Green Historic District
  • Knights of Columbus Museum
  • Frank Pepe Pizzeria

Where to stay new Haven

And, it’s only a mile away from Yale University and East Rock Park.

new haven where to stay

Amenities: The house is fully equipped with everything from toiletries, laundry facilities, and pet food bowls to parking and kitchen facilities.

Best place to stay New Haven

Special Features: There is onsite parking, a hot tub, a patio, a BBQ, and plenty of space to accommodate pets.

vacation home new haven

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Historic Stay

best place to stay in new haven

Location: This New Haven getaway is located less than half a mile away from:

  • Yale Repertory Theater
  • Chapel Street
  • Yale University Art Gallery
  • Grove Street Cemetery
  • Yale Center For British Art
  • Woolsey Hall
  • Schubert Performing Arts Center
  • Shubert Theater
  • Yale University
  • New Haven Green Historic District

new haven how to pay

Amenities: This historic getaway has free WIFI and parking, as well as a sun deck. There’s also a fully equipped kitchen and a lounge.

where to stay new haven

Special Features: Artistic decor, a luxurious, basin bathtub, a sun terrace with garden views.

New haven ct where to stay

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Omni New Haven Hotel at Yale 

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Location: Centrally located by Yale University, this hotel is has one of the most convenient locations in New Haven. It’s in walking distance to most of New Haven’s best attractions. You can find these New Haven sites in less than half a mile from the hotel:

  • Trinity Episcopal Church on the Green
  • Schubert Theatre
  • Schubert Performing Arts Center
  • New Have Green Historic District
  • Chapel Street
  • City Hall
  • Center Church Crypt
  • Yale University Art Gallery
  • Yale University

connecticut new haven hotel

Amenities: This hotel offers top notch amenities like:

  • Daily housecleaning
  • Room service
  • A hair/beauty salon
  • 24-hour desk
  • Concierge service
  • An onsite ATM
  • Pet-friendly rooms

new haven hotel

Special Features: As one of the most luxurious hotel options in New Haven, the Omni offers:

  • A spa
  • Fitness center
  • On-site coffee shop
  • Restaurant with dining menu
  • Buffet-style restaurant
  • On-site bar

new haven hotel

where to stay in new haven

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ArtLab Metro 280

best hotel new haven

Location: This centrally located hotel is less than a half mile from some of New Haven’s best attractions. These include:

  • City Hall
  • Chapel Street
  • Yale Center For British Art
  • Schubert Theatre
  • Yale University Art Gallery
  • Amistad
  • Trinity Episcopal Church on The Green
  • Schubert Performing Arts Center
  • New Haven Green Historic District

where to stay in new haven

Amenities: The general amenities here include:

  • Wifi
  • In-room coffee machine
  • Flat screen T.V in rooms
  • Some rooms have a lounge/sitting area
  • Equipped kitchen

where to stay new haven

Special Features: 

  • Modern, artistic decor.
  • Plenty of space.
  • Fitness center.
  • Bar and restaurant on-site.

Where to stay in new haven

Check Rates and Reviews.

If you want to visit New Haven, Connecticut for the weekend, especially from Philadelphia, there is plenty to do. And, with the varied options for accommodation, you’ll be sure to find something that fits your style.

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