Connecticut boasts a long history of robust and enjoyable Thanksgiving celebrations. The spectacular parades, winter festivals, and family-friendly marathon runs make the state among the most popular Thanksgiving vacation destinations. Near many Connecticut vacation rentals, you can attend tree-lighting ceremonies, view re-enactments of early Thanksgiving activities, partake in holiday ice skating, and feast on traditional cuisine. Here are the best Thanksgiving getaway locations in the state of Connecticut.

1. Stamford

The city of Stamford lies just 30 miles from Manhattan in the southwestern corner of Connecticut. The annual UBS Parade Spectacular, a celebration of Thanksgiving that runs through downtown Stamford, is one of the largest helium balloon parades in the United States. Besides giant colorful helium balloons of famous cartoon figures, the parade features marching bands and flamboyant floats. Spectators come from all over New England and other nearby states to view the show. Don’t miss watching the balloons come alive at the Balloon Inflation Party the day before.

Find vacation rentals near Stamford

2. Manchester

Manchester, which adjoins Hartford in central Connecticut, is home to the famous Manchester Road Race. Scheduled every year during the Thanksgiving season since 1927, this immense holiday event draws over 10,000 participants from all over the world. Although the race attracts Olympians and other world-class runners, a special area is marked off for people who want to walk the course, and children 12 and under can run in the Little Manchester Road Race. Many runners and fans dress up colorfully, and a competition chooses each year’s best costumes.

Find vacation rentals near Manchester

3. South Windsor

South Windsor lies along the Connecticut River just northeast of Hartford. Every year during the Thanksgiving holiday, the Wood Memorial Library and Museum hosts the Gingerbread House Festival, which is one of New England’s largest displays of gingerbread creations. Bakers, artisans, and homemakers construct mansions, fairytale castles, trains, and whole villages out of gingerbread and candy. The festival also has a Legend of Santa Claus display, a family photo area, and a shop where you can purchase gifts and delicious holiday treats. For an unforgettable Thanksgiving dinner, head for the historic Mill on the River for a special feast of turkey and trimmings.

Find vacation rentals near South Windsor

Find the perfect Connecticut vacation rental on is the world's #1 vacation rental search engine with over 10 million properties!

4. Essex

The town of Essex, located in south-central Connecticut near the mouth of the Connecticut River, hosts the famous Essex Steam Train. Thanksgiving weekend marks the commencement of the annual family-friendly Santa Special seasonal train excursions. Traditional decorations festoon the railway cars, and Santa and Mrs. Claus stroll along the aisles and visit each child, followed by Santa’s elves distributing gifts. In the station, take photos on Santa’s sleigh, send gift requests at Santa’s Post Office, and taste freshly-baked cookies at Klaus Kitchen.

Find vacation rentals near Essex

5. Hartford

Hartford, the capital of Connecticut, kicks off its annual Winterfest every Thanksgiving weekend at Bushnell Park. The outdoor ice skating rink is open to all for free skating, and rental skates and ice skating lessons are easily available. Winterfest also includes carousel rides, photo opportunities with Santa at the Pump House Gallery, displays of ice sculptures, and vendors offering tasty hot chocolate. For a delicious Thanksgiving dinner, try the slow-roasted turkey with stuffing and the pumpkin cheesecake dessert at the Capital Grill on Front Street.

Find vacation rentals near Hartford

6. Fairfield

The historic city of Fairfield lies on the coast of Long Island Sound. Since the early 1800s, the city’s residents stroll from house to house before Thanksgiving sampling pies. The Fairfield Museum and History Center commemorates this tradition at Ogden House, whose construction dates to 1750. Enjoy pie tasting along with candlelight tours of this fascinating structure. The museum also celebrates Thanksgiving with a performance of eastern Native-American songs and dances.

In nearby Stratford, join the Thanksgiving Day Turkey Day Trot, a 5K race through the downtown area. For a truly unusual Thanksgiving race, head to Trumbull, which adjoins Fairfield on the northeast, for the Cow Chip Cross Country Run. This unique event for all ages features a 3-mile loop through open cow pastures. Some participants dress up like farm animals, and organizers suggest that you wear old sneakers for your exuberant dash through the mud.

Find vacation rentals near Fairfield

7. Bethel

The town of Bethel, located just south of Danbury near the western Connecticut border, hosts its annual Winterfest during Thanksgiving weekend in its historic downtown area. Activities include horse-drawn carriage rides, a baking contest, live entertainment, and a visit by Santa in P.T. Barnum Square to light the town Christmas tree. Local restaurants provide free soup, and s’mores are available at a large outdoor fire pit. The Winterfest also schedules a Run Santa Run 5K race and a Kids Fun Run. After Winterfest, shop for gifts at the Holiday Marketplace in Santa’s Village at the Bethel Municipal Center.

Find vacation rentals near Bethel

8. Greenwich

Greenwich lies just north of New York City at the western end of Long Island Sound. Thanksgiving weekend is the start of the city’s Reindeer Festival and Santa’s Village. Bring the kids to view live reindeer, visit Santa, and ride on the Winter Wonderland Carousel and the North Pole Polar Express Train. Other attractions include face painting, balloon art, and holiday refreshments. After the Greenwich Turkey Trot, an easy 1-mile race in Bruce Park, all the participants receive medals. Enjoy a classic Thanksgiving meal at The National restaurant on Greenwich Avenue.

Find vacation rentals near Greenwich

9. Simsbury

Simsbury, a town in northern Connecticut, hosts a yearly event called Simsbury Celebrates during Thanksgiving weekend. Activities include trolley rides and train rides up and down Hopmeadow Street as well as a parade featuring the arrival of Santa on a fire truck. Among the other attractions are a gingerbread house exhibit, pony rides for kids, and a toymaker’s workshop. The culmination of the event is a spectacular display of fireworks accompanied by holiday music.

Find vacation rentals near Simsbury

Ready to go? Check out these amazing Connecticut vacation rentals on