One Weekend In New Haven, Connecticut: The Ultimate 3-Day New Haven Itinerary
The second largest city in Connecticut, New Haven is known as the home to Ivy League institution Yale University and as the “Pizza Capital of the World”. Located on the shores of Long Island Sound, New Haven is rich with historical sites, museums, outdoor recreations, and tons of activities the whole family will enjoy. I’m excited to share the ultimate 3-day New Haven itinerary, it’s the best way to spend one weekend in New Haven!
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Side Note: This New Haven weekend guide was written by Jenn, a local of Fairfield County Connecticut. This way, you can ensure you are reading the best and most accurate weekend in New Haven. Locals know best!
Table of Contents
Getting to New Haven, CT
New Haven is an easy, two-hour drive on Interstate 95 from both New York City and Boston. Most parts of downtown New Haven city are quite walkable, but public buses are available via CT transit.
Tweed New Haven Airport offers flights to 20 domestic, East Coast destinations plus Chicago, and Amtrak offers daily service to Union Station in New Haven on the East Coast corridor route.
Best Time to Visit New Haven
New Haven is beautiful any time of year. In October and early November, the fall foliage is vibrant on the New Haven Green and public parks and the summer offers the opportunity to enjoy Lighthouse Point Park and nearby Silver Sands State Park (Milford) and Hammonasset Beach State Park (Madison) beaches.
New Haven hosts several popular festivals and annual events throughout the year, including the St Patrick’s Day Parade in March, the Cherry Blossom Festival in April, the International Festival of Arts and Ideas in June, and Fantasy of Lights in November and December.
Average New Haven Seasonal Temperatures:
- Winter (Dec-Feb): 41/27, 6.5 days of rain
- Spring (March-May): 60/42, 7.5 days of rain
- Summer (June-Aug): 83/64, 6 days of rain
- Fall (Aug-Nov): 65/47, 5 days of rain
Peak Fall Foliage: October 3rd-November 8th
Where to Stay in New Haven
There are several places to stay throughout the downtown New Haven area. Popular spots include the Courtyard Marriott, Graduate New Haven, and the newly opened Hotel Marcel.
For a splurge, check out the Omni New Haven at Yale (steps from the university and tons of museums and restaurants) and the Study at Yale to stay literally on campus.
A quick 20-minute drive north includes popular resorts Water’s Edge Resort and Spa and Madison Beach Hotel, both with private beaches.
New Haven Weekend Itinerary: How to Spend 3 PERFECT days in New Haven, CT
It’s time! Here’s the perfect way to spend 3 days in New Haven.
Day 1 in New Haven
Morning:
Grab a healthy breakfast at Claire’s Corner Coppia, which offers a wide variety of homemade pastries, sweet treats, and full meals all day.
Then take a quick walk through campus on your way to the Yale University Art Gallery, free and open to the public Tuesday through Sunday. Check out the tomb of John Trumbull buried beneath the stone floor on the first floor and the sculpture terrace, which also offers great views of the city.
The Yale Center for British Art, typically free and open to the public but currently closed in 2024 for renovation, is located across the street and is the oldest museum, outside of the United Kingdom, dedicated to British art.
Afternoon:
Make a quick stop at the Beinecke Rare Book and Manuscript Library, which touts over one million books and thousands of maps, photographs, and artwork in its collection. The first floor is open to the public (and free!); be sure to peek down into the sculpture garden outside the main entrance.
To have bragging rights for having eaten at the “Birthplace of the Hamburger Sandwich”, head to Louis’ Lunch. Then spend the afternoon shopping at the Shops at Yale, which include favorites J. Crew, LL Bean, and Atticus Bookshop.
Evening:
There are plenty of dinner options to suit any palette (Harvest Wine Bar for an impressive wine list, Heirloom at the Study at Yale for farm-to-fork, and Union League Cafe for a special occasion).
After dinner, see if your group can “escape” the challenges at Escape New Haven, which offers four different themed indoor experiences and even three outdoor adventures throughout the city.
Day 2 in New Haven
Morning:
Grab a coffee at Common Grounds (the Wall Street location) and head to the newly renovated Yale Peabody Museum (set to reopen in early spring 2024) for 10 curated exhibits featuring everything from dinosaurs to gems and minerals to birds and bugs with dozens of remodeled dioramas and hands-on activities for all ages.
Afternoon:
After feeding your brain with knowledge, feed your stomach with an “apizza” tour of some of the most popular spots for pizza. It’s worth the wait (none of these spots accept reservations) at Pepe’s and Sally’s, both located on Wooster Street, known as the “Little Italy” of New Haven, and nearby Modern, and BAR.
Then work off the pizza lunch with a short hike to Judge’s Cave.
Evening:
Walk over to Barcade and play over 40 different arcade games and pinball machines. There’s over two dozen beers on tap. Winner has to buy everyone ice cream from the famous Arethusa Farm Dairy– it’s a quick walk from Barcade.
Day 3 in New Haven
Morning:
To get one more view of the city, head to East Rock Park and hike the path to the top of the park to the Soldiers and Sailors Monument honoring New Haven soldiers from the Revolutionary War through the Civil War.
Seasonally, visitors can climb inside the monument to an observation deck. The summit offers beautiful views of the city and Long Island Sound. Bonus points if you can get here at sunrise!
Afternoon:
Grab a take-out picnic from Archie Moore’s (make sure to grab a few of their famous buffalo wings) and head to Lighthouse Point Park. It’s an 80+ acre park that includes a lighthouse, carousel (open seasonally), walking trails, playground, seasonal splash pad, and plenty of space to spread out and soak in the sun and surf.
Evening:
The popular Coastal Connecticut Shoreline runs just east of New Haven and includes the waterfront towns of Westbrook, Madison, and Old Saybrook. Here, you’ll find wine vineyards, outlet shopping, and tons of waterfront dining!
Some activities along the coastline include a cruise around the Thimble Islands, or watching the sunset at Hammonasset Beach State Park. Or, you can head inland to Old Lyme and Essex where you’ll find historic museums like the Florence Griswold Museum and Connecticut River Museum.
Unfortunately, won’t have time for all the coastal festivities, so I recommend picking one and then taking time to enjoy a dinner at a nearby waterfront restaurant.
Other Tips to Know Before Visiting New Haven:
- Out-of-city visitors will need to pay a daily rate at local beaches and parks
- Pay close attention to parking meters and timing when parking on city streets. Check here for information on parking garages and rates.
- Check hours for restaurants and museums- several are closed on Mondays.
More Things to Do in New Haven
- Ghost Tour: Delve into the spooky side of New Haven with a ghost tour. These tours offer a blend of historical facts and local ghost stories, leading participants through historic streets and landmarks under the cloak of night. It’s an intriguing way to learn about the city’s past residents and their haunting tales.
- Watch a Show at Yale Repertory Theater: The Yale Repertory Theater is renowned for its high-quality productions that often feature emerging and established playwrights, directors, and actors. Attending a show here offers a chance to see new works and classic plays reimagined by talented artists. It’s a cornerstone of New Haven’s vibrant arts scene and provides an enriching cultural experience.
- The PEZ Visitor Center: For something uniquely different, visit the PEZ Visitor Center located nearby in Orange, CT. This colorful and interactive museum is dedicated to all things PEZ, showcasing the history of the iconic candy dispenser and its many designs over the years. The center includes a viewing gallery of the PEZ production area, a vast collection of PEZ memorabilia, and the world’s largest PEZ dispenser. It’s a fun and nostalgic experience for both children and adults
- Shubert Theater: Catch a Broadway tryout or a live performance at this historic theater known for hosting world and American premieres
Where (else) to Eat in New Haven
If you get tired of pizza (is that even possible?), here’s a list of other delicious restaurants in New Haven!
- Olea: Offers authentic Spanish and Mediterranean dishes in downtown New Haven, celebrated for its delectable food and fine wine selection.
- Zinc: This New American restaurant is ideal for enjoying exquisite farm-to-table cuisine. It’s known for its stylish decor, full-service bar, and fantastic menu, making it a great spot for birthdays.
- Barcelona Wine Bar: A Spanish restaurant with an ever-changing menu, offering a vibrant atmosphere, delicious tapas, and an impressive wine selection.
- Atticus Bookstore Cafe: More than a bookstore, this cafe offers tasty American cuisine, a cozy vibe, freshly brewed coffee, and an extensive collection of books.
- Shell & Bones Oyster Bar and Grill: An award-winning seafood restaurant located on the waterfront, known for its fresh seafood dishes, steaks, and stunning views
Weekend in New Haven Map
Here’s a map to help you plan the perfect weekend in New Haven!
Is New Haven Worth Visiting?
Yes! New Haven is 1000 percent worth visiting and one weekend is definitely not enough to see it all. Fellow fans of Gilmore Girls will especially love immersing themselves in the small-town charm and pizza-lovers will delight in the city’s iconic pizza scene. With the help of this 3-day New Haven itinerary, you will surely have the best time in this Northeastern gem.
About the Author!
Jenn Record, founder and editor of Coast2CoastwithKids.com, grew up in Boston but has lived in Fairfield County Connecticut for the past 20+ years and frequently explores all corners of Connecticut. A high school English teacher, she enjoys road-tripping throughout the country with her husband and children during school breaks and the summer.
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