Roundups > Explore our Two-Day Tour of Greater New Haven
Explore our Two-Day Tour of Greater New Haven
From history and cruises to shopping, live music, and more, there’s so much to see and do in New Haven County. To help you plan your trip, we’ve provided this handy guide showing the best places to explore throughout the area.



Day 1 | Elm City Tour
Stop #1: Discover the history of New Haven and view exquisite architecture, public art and campus life during the walking tours at Yale University Visitor Center, New Haven.
Stop #2: Explore the Blessed Michael McGivney Pilgrimage Center in New Haven. This museum, founded in 1882, that celebrates the life of Father McGivney and the history and art of Catholicism.
Lunch: New Haven’s Little Italy Wooster Street is home to some of New Haven’s, and the world’s best-known pizza eateries.
After lunch, choose Option 1 or 2 for your afternoon destinations
Option 1 | Historic Chapel Street Art and Shops
Stop #3: Visit two of Yale’s world-renowned art museums Yale Center for British Art and the Yale University Art Gallery. They are free and open to the public.
Stop #4: Take a stroll down the bluestone sidewalks and enjoy the Shops at Yale in New Haven that are lined with numerous independent boutiques and national retailers.
Option 2 | History Explorers
Stop #3: Visit Elm City’s civic and art museum, New Haven Museum in New Haven. Showcasing history, geography, industry, neighborhoods, ethnic and religious heritage and the Maritime and Amistad Galleries.


Day 2 | Shoreline Sun & Fun Tour
Stop #1: Marvel at the world’s largest collection of PEZ memorabilia and the PEZ Candy Visitor Center. Located at the actual factory on Orange where the candy is made.
Stop #2: Visit the Shore Line Trolley Museum in East Haven and ride the antique streetcars along a scenic, century old trolley line through marshes, woods and nature preserves.
Lunch: Try a seafood hotspot in one of the historic shoreline towns.
- Bill's Seafood Restaurant
- M&J Beach Grille and Seafood
- Abbott's Lobster in the Rough
- S&P Oyster Company
- Lenny and Joe's Fish Tail
- Stowe's Seafood
- The Restaurant at Rowayton Seafood
Stop #3: Ride back in time with old stories as well as beautiful views of the 365 small islands aboard one of the Thimble Island Cruises.
Stop #4: Stroll through a charming village-like setting at Clinton Crossings Premium Outlets, where you will fi nd 70 designer and name-brand outlets, that offer savings of 25% to 65%.


Other Nearby Options
End your evening at the theater or enjoy New Haven’s lively nightlife:
Add a winery tour and tasting to your visit:
- Bishop’s Orchards & Winery, Guilford
- Chamard Vineyards, Clinton
- Gouveia Vineyards, Wallingford
- Paradise Hills Vineyard & Winery, Wallingford
- Savino Vineyards, Woodbridge
Visit a popular annual event or festival:
- Durham Agricultural Fair
- International Festival of Arts and Ideas
- Lyman Orchards Corn Maze
- Milford Oyster Festival
- Seasonal Bird Walks at Hammonasset Beach State Park