Things To Do In Stratford CT: Top 23 Most Unique Spots | Stanton House Inn

Blue jay on a roof at Academy Hill

Stratford, Connecticut, is a charming town filled with rich history. Plus, you can’t forget about its picturesque outdoor attractions and unique dining experiences. The city awaits your visit!


With so much to see and do, there won’t be a moment you’re not busy in Stratford—unless you want to be. From scenic parks and historic sites to mouthwatering cuisine and special treasures, you’ll never run out of things to do here. 


The beauty of Stratford is that you can stay plenty busy indoors or outdoors; the choice is yours! It has the largest antique dealer marketplace and a quite historic downtown area, among other highlights. You’ll find plenty to do by yourself or with your friends and family.


So, are you ready to dive into the delights of the best things to do in Stratford, CT? Let’s get into it:


Quick Hits:

  • Explore Stratford, CT’s outdoor activities & historic sites.
  • Unwind at Boothe Memorial Park and explore Roosevelt Forest’s trails & ponds.
  • Enjoy Short Beach’s recreational activities, Lordship Seawall views, and the Connecticut Audubon Society Coastal Center for birdwatching.

things to do in stratford ct map Things to Do in Stratford CT: Top 23 Most Unique Spots
Map design by Stanton House Inn

A Brief History of Stratford, Connecticut

1909 postcard of the Stratford Library

Stratford’s foundation was laid in 1639 by Puritan leader Reverend Adam Blakeman and William Beardsley. It was an era known as the Great Migration, as European settlers switfly established colonies in northeastern America. Locals initially called their new town Cupheag in 1640. They soon adopted a more poetic name inspired by Shakespeare’s birthplace in England, Stratford-upon-Avon.


In the early days, Stratford was a unique blend of church and town leadership under Reverend Blakeman. The aim was to create idealistic religious outposts, shielded by wilderness (and an ocean) from the interference of kings, parliaments, or other secular authorities.


Blakeman’s rule ended with his death in 1665. As the second generation of Stratford matured, they began to challenge the town founders’ austere lifestyle. Over time, standard colonial administration replaced the utopian nature of early Stratford. By the late 17th century, the Connecticut colonial government administered Stratford. That said, many descendants of the original Puritan families remain in Stratford today. They often intermarry within the original group of 17th-century Pilgrim families, of which U.S. President Gerald Ford is a descendant.


Stratford was one of the two main settlements in southwestern Connecticut, the other being Fairfield, CT. As such, these towns seeded many others here and further west. Stratford is home to Connecticut’s first Anglican church, founded in 1707 and first ministered by Rev. Dr. Samuel Johnson. Settlers from Stratford founded other American cities and towns, including:



The 19th and 20th centuries witnessed the construction of a trolley connecting Lordship to Bridgeport in 1914, linking the resort area to the neighboring city.


Outdoor Things to do in Stratford CT

A picture of people kayaking in the Housatonic River, one of the top things to do in Stratford CT

Nature enthusiasts and history buffs alike will find Stratford, CT, the perfect destination for a fun-filled getaway. Its beautiful parks, stunning beaches, and captivating seaside views are simply amazing. There’s no shortage of exciting outdoor activities to enjoy.


Hit Up the Hikes

The hikes are especially wonderful for beginners in this area. The trails in Stratford are all considered “easy.” Now, easy can mean a lot of things to a lot of people. But here, it mostly talks about incline.


On a hike in Stratford, you can expect the elevation to remain pretty even throughout. Some of these trails will certainly test your endurance when it comes to distance, however. The trails range from just under a mile up to just over 4 miles. Some are along the water, while others are more wooded.


Want a quick breakdown? We’ve got you covered! We’re arranging this list from shortest to longest distance:


  1. Roosevelt Forest Short Loop: .9 miles. Approx. 20 min.
  2. Stratford Seawall: 1.6 mi. Approx. 30 min.
  3. Roosevelt Forest Loop: 2.9 mi. Approx. 60 min.
  4. Sikorsky Estuary Trail: 3.3 mi. Approx. 1h 15 min.
  5. Long Beach and Pleasure Beach: 4.2 mi. Approx. 1h 30 min.


Relax with A Little Birdwatching

For the birdwatchers out there, Stratford has you covered! 


The Connecticut Audubon Society Coastal Center at Milford Point is a must-visit location to learn even more about the hobby and area.


You’ll want to check out the adjoining 8-acre Smith-Hubbell Wildlife Refuge and Bird Sanctuary. It’s open daily, year-round, from dawn to dusk.


It’s said that over 3000 bird species have been witnessed in this area. So, with a good pair of binoculars and a fair amount of time, you’ll be able to learn a lot about the area’s wildlife.


Boothe Memorial Park

Boothe Memorial Park

Boothe Memorial Park is a 32-acre public park that offers a blend of history and nature for you to explore. The park is home to several fascinating historic buildings, including:


  • A miniature lighthouse
  • A windmill
  • A trolley station
  • An Americana museum


All of these spots are nestled within the beautiful Putney section of Stratford. 


As you wander through the park, don’t forget to stop and smell the roses at the award-winning rose gardens. You can also immerse yourself in the past by exploring the genealogy library.


Throughout the spring and summer months, Boothe Memorial Park comes alive. It hosts outdoor concerts and Shakespearean plays, making it the perfect destination for a family outing or a romantic date. Feeling hungry? Grab a bite to eat at the nearby Beach House Grill to complete your visit to this historic gem.


Roosevelt Forest

Woodland in Stratford, CT

Discover the beauty of nature at Roosevelt Forest, a serene oasis featuring trails, ponds, wetlands, and a diverse array of birdlife. Some of the beauty of this park is its facilities! It includes picnic benches, cooking pits, and playgrounds, perfect for a family out. It can also be fit for a day alone reading or as a peaceful retreat with friends.


You may prefer hiking, wildlife-watching, or even snowshoeing and cross-country skiing. Sure, some of these activities are season-permitting. But good news! Roosevelt Forest has something for everyone. Keep your eyes peeled for small mammals, deer, amphibians, and reptiles as you explore this natural wonderland.


Short Beach

Short Beach, a beautiful municipal beach, offers a variety of recreational activities for visitors to enjoy. You can stop by for some swimming and fishing, sailing lessons, and a recreation complex. There’s something for everyone at this popular destination. Plus, with handicapped access, everyone can experience the beauty of Short Beach and its surrounding nature.


As you stroll along the water’s edge, keep an eye out for the beach’s unique wildlife, such as horseshoe crabs, piping plovers, and nesting terns. Short Beach is not only a place to unwind and have fun, but it’s also a haven for nature enthusiasts.


Like most Connecticut beaches, Short Beach is residents-only in the summer. You can buy a pass before you go, though.


Lordship Seawall

Looking for breathtaking views of Long Island Sound? Look no further than the picturesque Lordship Seawall. This stunning location offers a chance to marvel at the maritime traffic, relax on the beach, and soak in the un-touristy atmosphere.


When hunger strikes, head over to Riley’s by the Seawall. This delightful restaurant offers dishes like:

  • Maryland crab cakes
  • Scampi Flatbread
  • Sesame-Crusted Tuna Salad
  • Lobster Rolls


With its beautiful scenery and delicious dining options, Lordship Seawall is the perfect spot to unwind and indulge.


Connecticut Audubon Society Coastal Center at Milford Point

For birdwatching enthusiasts, there’s one spot you must visit. The Connecticut Audubon Society Coastal Center at Milford Point! This birdwatching preserve boasts informative exhibits and observation platforms. Plus, there is a plethora of bird species to discover.


As you explore the center, keep an eye out for some cute creatures during the late summer. Intrigued? Be sure to look for American oystercatchers, piping plovers, ospreys, and other waders. And during the winter months, you might even spot the elusive snowy owl.


You can be an experienced birdwatcher or a curious novice. Either way, the coastal center is one of the best things to do in Milford, CT.


Long Beach

Long Beach is a 1.5-mile coastal barrier island that offers a serene escape for beach lovers. Access to certain areas is restricted to protect rare birds. However, visitors can still enjoy swimming, sailing, and fishing at this beautiful location.


With its pristine sands and tranquil waters, Long Beach is the perfect spot to unwind and connect with nature.


Immerse Yourself in Stratford’s Historic Sites

Historic sites in Stratford, Connecticut

Delve into Stratford’s rich past by visiting its fascinating history museums. Stratford’s heritage comes alive through its captivating landmarks.


Whether you’re a history buff or simply curious about the town’s roots, these sites offer a glimpse into Stratford’s storied past.


National Helicopter Museum

The National Helicopter Museum is a treasure trove of information. Here, you can learn so much about the history and development of rotary-wing aircraft. It boasts an extensive collection of images and objects. These help the museum tell the fascinating story of the aviation and helicopter industry. You’ll be able to learn from early innovators, such as Leonardo da Vinci and modern helicopters. Simply put: It’s such an impressive museum.


Exhibits include models of aircraft from Bell, Boeing, Robinson Helicopter, and Kaman Aircraft. You can also check out a Sikorsky S-76 helicopter cockpit and mini gas turbine engines from the Boeing CH-47 Chinook and Huey. All were designed with precise metric and imperial units.


Make sure to try the flight simulator for an immersive and informative experience!


Connecticut Air & Space Center

Road through Stratford, Connecticut

This small museum occupies the former Stratford Army Engine Plant. So, for directions, it’s right across the street from the Sikorsky Memorial Airport. 


The Connecticut Air & Space Center showcases vintage aircraft and aviation-related artifacts. Each item pays tribute to Connecticut’s rich aerospace history. 


As you wander through the center, you’ll find nine different aircraft, including a 1945 Vought/Goodyear FG-1D Corsair. Plus, you’ll witness the world’s first supersonic jet trainer, a 1961 Northrop T-38A Talon.


The museum opened in 1998, following the closure of the Stratford Army Engine Plant. It is housed in two buildings that were previously part of the plant complex. As such, it is one of the few museums in the United States in a genuine WWII aircraft factory.


In addition to the impressive aircraft displays, the center has even more. It also houses exhibits that tell the story of the Stratford Army Engine Plant’s history. If you’re an aviation enthusiast, the Connecticut Air & Space Center is a must-see destination.


Captain David Judson House

Judson House, managed by the Stratford Historical Society

The Captain David Judson House is a stunning Georgian-style house in the Academy Hill Historic District. It transports visitors back in time with its meticulously restored rooms filled with period furniture. It was built for Captain David Judson, the head of Stratford’s militia. 


Today, this historic home is listed on the National Register of Historic Places. It’s an important part of the town’s history, which includes notable figures like William Samuel Johnson.


The house is currently managed by the Stratford Historical Society. Captain David Judson House offers self-guided tours, allowing you to immerse yourself in Stratford’s past. You’ll be able to check out fascinating collections of Chinese porcelain and the beautiful crown chair. 


Every corner of this house reveals a glimpse into the lives of those who once called it home.


Ruby and Calvin Fletcher African American History Museum

The Ruby and Calvin Fletcher African American History Museum can be found in Stratford. This is the first museum of its kind in Connecticut. It is dedicated to preserving and highlighting history through the lens of black experiences. This museum showcases a remarkable collection. Artifacts, photos, and documents collected by Ruby and Calvin Fletcher are easily the highlights.


Maybe you’re a history enthusiast or simply curious about the stories of this community. Regardless, history museums like this one offer a unique and inspiring experience.


Perry House

Built by Benjamin Beach in 1690, the Perry House is a symbol of Stratford’s Colonial heritage and a testament to the town’s rich history. Today, the Perry House Foundation manages this historic building. 


It is used as a base for programs that increase public awareness of Stratford’s heritage. It also offers self-guided tours for visitors to explore its fascinating past.


In addition to its historical significance, the Perry House is great for gatherings. It also serves as a versatile venue for special events, such as weddings, parties, fundraisers, and corporate functions. It can accommodate up to 100 guests, making it suitable for many festivities. 


Plus, it has some beautiful architecture and a storied past. The Perry House offers an unforgettable experience for visitors and event-goers alike.


Stratford Veterans Museum

Housed at Boothe Memorial Park, the Stratford Veterans Museum stands in honor. It also recognizes the sacrifices of Stratford’s veterans from the Revolutionary War to the present day. It has some captivating exhibits and dioramas. Through these items, the museum tells the personal stories of those who served. It also helps educate school-age children about the importance of their sacrifices.


A visit to the Stratford Veterans Museum is a poignant reminder of the bravery and dedication of the men and women who have served our country.


Sterling House

Sterling House is a historic mansion turned community center. It has been offering programs and services to everyone in Stratford since 1932. 


Located just off Elm Street, Sterling House provides a welcoming space for residents of all ages. It’s a wonderful place to learn, grow, and connect through offerings. Some of these include art classes, music lessons, dance classes, and community events.


Here, you can pick up a new hobby or meet new friends. Sterling House offers a variety of opportunities to engage with the Stratford community.


Unique Dining & Drinks in Stratford, CT

Unique dining and drinks in Stratford, Connecticut

Foodies and craft beer lovers will find plenty to savor in Stratford, CT, and nearby cities.


With a wide range of dining options and unique libations, Stratford, CT, offers a culinary adventure you won’t want to miss.


Two Roads Brewing Company

Two Roads Brewing Company in Stratford offers a diverse range of craft beer, including year-round, seasonal, Tanker Truck Sours, and limited-release brews. Popular brews include:

  • Ol’Factory Pils
  • Worker’s Comp Farmhouse Ale
  • Little’Heaven Session IPA
  • No Limits Hefeweizen

Visitors can enjoy a guided brewery tour and beer tastings in the modern tasting room. With an impressive selection and welcoming atmosphere, Two Roads Brewing Company is a must-visit destination as one of the best breweries in CT.


Gaetano’s Deli

Gaetano’s Deli is a family-owned deli and caterer in Stratford, CT, offering authentic Italian cuisine for over 20 years. With locations in Stratford, Westport, and Shelton, customers can enjoy imported charcuterie and cheeses, gourmet sandwiches, and delicious salads. Gaetano’s Deli also provides catering services for events of all sizes, catering to guests of all sizes. The mouthwatering menu and exceptional service make it a beloved local gem in Stratford, CT.


Station House Wine Bar and Grill

Station House Wine Bar and Grill, located in Stratford Train Station, offers a unique and eclectic dining experience with a diverse menu of traditional Italian cuisine and artisan Japanese sushi. The restaurant also features a New York City-style bar and a lively entertainment schedule, including live music, happy hour, trivia nights, and wine and beer tastings. Whether for a romantic dinner or a fun night out with friends, Station House Wine Bar and Grill is the perfect spot for great food and memorable moments.


Wells Hollow Creamery

Wells Hollow Creamery in Stratford, CT offers over 50 ice cream flavors, sundaes, and shakes, including “no fat” options. The family-run dairy farm offers a tour of the farm, allowing visitors to see cows, goats, and chickens up close. With its delicious ice cream and charming atmosphere, Wells Hollow Creamery is a must-visit destination for ice cream lovers and their families.


Open Door Tea

Open Door Tea is a family-run cafe that offers over 100 drinks and pastries since 2016. The cozy atmosphere is complemented by a variety of teas, custom blends, and herbal wellness blends. The cafe also offers organic pastries, bars, and treats. For a relaxing outing, try their quiche. Open Door Tea is one of the best tea rooms in Connecticut for a relaxing outing.


Unique Shopping in Stratford, CT

Unique shopping in Stratford, Connecticut

For a shopping experience like no other, head to Stratford, CT. This town is home to the Stratford Antique Center, a large multi-dealer store with over 200 dealers offering a wide selection of antiques. You may be searching for a unique treasure or simply browsing. Either way, you can spend hours exploring this spot. There are some truly fascinating finds at this one-of-a-kind shopping destination.


The Stratford Antique Center is a great place to find unique items from all over the world. There are plenty of antiques, collectibles, and vintage items. You’re sure to find something special! From furniture to jewelry, there’s something here to fit your style and budget.


Shop at the Stratford Antique Center

The Stratford Antique Center is an antique lover’s paradise. It features over 200 dealers selling a vast array of antiques. You can spot furniture, jewelry, art, and collectibles. As you wander through this expansive store, you’ll be transported back in time. Here, you can discover unique treasures and pieces of history at every turn.


Located in Fairfield County, the Stratford Antique Center is the perfect destination for a leisurely shopping day. Or, you can hunt for a perfect statement piece for your home. It has an ever-changing inventory and friendly dealers. That’s what makes this antique center a must-visit shopping experience in Stratford, CT, and one of the best antique shops in CT.


Hotels, Inns, and Places to Stay in Stratford, CT

Long Island Sound from Lordship in Fairfield County

Stratford is a mere stone’s throw away from our humble abode in Greenwich, Connecticut. A swift 30-minute drive along Interstate 95 or the Merritt Parkway will get you there. It’s an ideal spot for a Connecticut day trip. Make it a Sunday adventure and you can also explore some of the things to do in Bridgeport, CT.


When it comes to unique accommodations in Stratford, there’s one place that takes the cake:


Surfside Hotel

What started as popular restaurants in Cos Cob, CT, Little Tavern, is expanding into quite a local legend in hospitality. The Surfside Hotel is all that’s left of the resort scene that used to thrive in the Lordship borough of Stratford. And it’s a great spot, as the only beachfront boutique hotel in southern Connecticut.


Looking for a cozy place to rest near Stratford? You’ve got a few stellar options from the list of the best bed and breakfasts in Connecticut, right in Fairfield County:





Discover Even More Things to Do Close to Stratford

Need more to plan a day trip?


Not to worry!


Stratford and nearby Bridgeport, CT, are great spots to poke around on a weekend afternoon.


If you’re looking for parks nearby, checkout:


And historic buildings and sites to explore close to Stratford include:


Be sure to read our guide to the most unique things to do in Fairfield County, Connecticut before you go.


We hope you enjoy wherever the road takes you!


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