Port Chester

Day Trips

Make the most of your day with our curated plans, packed with Port Chester's hidden gems and unique experiences!

day 1
Explore Port Chester
morning
:

Start your day with a delicious breakfast at a local café. Afterward, take a stroll along the waterfront to enjoy the fresh air and beautiful views.

afternoon
:

Visit the Port Chester Historical Society to learn about the town's rich history. Enjoy lunch at one of the various international restaurants offering diverse cuisines.

evening
:

Catch a show at the Capitol Theatre for a night of entertainment. After the show, wind down with drinks at a nearby bar.

day 2
Nature Day in Port Chester
morning
:

Begin your day with a visit to Lyon Park for a relaxing morning walk or jog. Enjoy breakfast at a nearby diner known for its hearty portions.

afternoon
:

Spend your afternoon at the nearby Chester Park, indulging in a picnic. This is a great time to relax, read a book, or play some outdoor games.

evening
:

Explore a casual dining spot in town for dinner. Consider wrapping up the day with a visit to a local ice cream shop for dessert.

day 3
Art and Culture
morning
:

After breakfast, head to the Puerto Rican Arts Alliance to immerse yourself in local art. You can also explore nearby galleries showcasing diverse artists.

afternoon
:

Have lunch at one of Port Chester's vibrant eateries that feature local flavors. Spend the afternoon visiting the nearby Knapp House and its charming exhibits.

evening
:

Dine at a fantastic restaurant that offers cuisine from around the world. Enjoy a quiet evening walk to digest and see the town lights.

day 4
Shopping Spree
morning
:

Fuel up with breakfast at a trendy café before hitting the shops. Explore local boutiques for unique souvenirs and gifts.

afternoon
:

Take a break for lunch at a popular bistro. Continue your shopping adventure at the nearby malls for more options and sales.

evening
:

Have dinner at a local grill to refuel after a day of shopping. Consider checking out a local movie theater for a fun evening flick.

day 5
Culinary Exploration
morning
:

Start with a coffee and pastry at a beloved local bakery. Participate in a cooking class to learn about and prepare regional dishes.

afternoon
:

Enjoy the lunch you prepared in the class. Afterward, visit some local farms or markets to see where the ingredients come from.

evening
:

Savor dinner at a restaurant renowned for its unique twists on classic dishes. Conclude your foodie day with a dessert from a nearby confectionery.

day 6
Outdoor Adventure
morning
:

Get an early start with breakfast at home or a nearby café, then head to the waterfront for some kayaking. Enjoy the tranquility and natural beauty of the area early in the day.

afternoon
:

Return for a relaxed lunch at a lakeside restaurant. Consider hiking in a nearby park for some scenic views and fresh forest air.

evening
:

Enjoy a casual dinner at a pub while discussing the day's adventures. End the night with a nightcap at a local bar with live music.

day 7
Festival Day
morning
:

Join a local breakfast event or festival kickoff for a memorable start. Enjoy unique local dishes and performances.

afternoon
:

Engage in different activities during the festival, from crafts to games. Enjoy delicious street food offerings for lunch.

evening
:

Cap the day with a spectacular final event at the festival, featuring live entertainment. Wind down with a midnight snack from a food truck.

day 8
Learning Day
morning
:

Enjoy a light breakfast at a cozy café, then head to the Port Chester Library. Spend the morning reading or participating in a workshop.

afternoon
:

Savor lunch at a delightful eatery nearby. Attend a lecture or community program of interest in the afternoon.

evening
:

Wrap up your day with a cup of tea at a local tea house to relax and discuss what you've learned.

day 9
Beach Getaway
morning
:

Start your beach day with breakfast at a waterfront café. Pack your beach essentials for a fun day in the sun.

afternoon
:

Enjoy a day of sunbathing, swimming, or beach volleyball at a nearby beach. A packed lunch can keep your energy up for all the activities.

evening
:

Head back to Port Chester and have a seafood dinner at a restaurant with views of the water. End your night with a beach bonfire if there's one organized.

day 10
Sports Day
morning
:

Have breakfast at a popular sports bar to fuel your day of fun. Head over to the local sports complex for games or matches.

afternoon
:

Enjoy lunch at a food stand or café within the sports complex. Attend afternoon games featuring local teams for more local sports action.

evening
:

Celebrate with dinner at a restaurant with a sports vibe to conclude your sports-themed day. Relax and recount the highlights of the day with fellow fans.

Discover Port Chester

Read more in our Port Chester 2024 Travel Guide.

Port Chester Travel Guide