Leap Year of the Holiday Weekend Last Updated: January 2022

Who doesn’t love a long weekend? It gives us an extra day to rest, play or get away – and in 2020, it seems we have Leap Day to thank for more time to celebrate. This extra day in the year has rearranged our calendar to create three more long weekends and puts holidays like Valentine’s Day and Halloween on Fridays or Saturdays. Cinco de Mayo even falls perfectly on a (taco) Tuesday! For maximum celebration, we’ve put together a list of exciting ways to enjoy your extra holiday weekends in 2020.

Valentine’s Day on a Friday

With Valentine’s Day on a Friday this year, we’re given the opportunity to get away – or at least stay out as late as we want.

Whisk them away to Greenwich’s luxurious Homestead Inn for a romantic weekend trip. While you’re there, treat yourself to a decadent meal at Homestead Inn's Thomas Henkelmann's Restaurant. If weather permits, stroll down Greenwich Avenue, but if weather keeps you indoors, perhaps try a couples massage at the Spa at Delamar Greenwich Harbor – or stay overnight too! If you're hungry for something exquisite, taste the delicious dishes at l’escale or the eye-catching French American cuisine at Meli-Melo.

For a getaway in the northwest corner, the Manor House Inn is offering a Valentine’s Day Romantic Escape package (February 13-16) that includes six chocolate covered strawberries and a complimentary half-bottle of champagne in your room upon arrival, and a delicious full breakfast delivered to your room.

For romance by the water, stay overnight and take advantage of the breathtaking sunrises that Saybrook Point Resort & Marina is known for.

If you’re looking to enjoy your Friday Valentine’s with a fun night out, try these fun places to dance or catch a show at one of Connecticut’s hottest live music venues like Infinity Hall in Norfolk, Ridgefield Playhouse in Ridgefield, or Black-Eyed Sally’s in Hartford.

Cinco de Mayo on a (Taco) Tuesday

While Cinco de Mayo does not fall on a weekend like most 2020 holidays, it does happen to land on the unofficial day to celebrate some of Mexico’s most popular cuisine: Taco Tuesday.

If you’re looking to celebrate Mexican culture with a delicious meal, try some of these great spots.

July 4th Long Weekend

With the Fourth of July falling on a Saturday, most organizations will observe it on Friday, giving Independence Day weekend an extra day of freedom.

If you’re looking to make the most of this summer holiday with a getaway, you might try a weekend of waterfront bliss at the Madison Beach Hotel, complete with a private beach, bicycle rental and spa . While you’re there, grab a bite at Elizabeth’s Café or flavorful meal at Café Allegre, followed by some summery scoops at Ashley’s Ice Cream and an outing to downtown Madison.  

For a different type of waterfront escape, spend the weekend in Mystic at The Whaler’s Inn or the Inn at Mystic. While you’re there, rent a rowboat or sailboat at Mystic Seaport Museum and discover marine life at Mystic Aquarium, including New England’s only beluga whales, the endangered African penguin, rescued seals and colorful fish. Be sure to leave time in your trip to explore the lively streets of Downtown Mystic, lined with boutiques, fudge and ice cream shops, and plenty of incredible restaurants including the award-winning Oyster Club.

Halloween on a Saturday

It’s not a trick – Halloween is on a Saturday this year. Treat yourself to a spooky day of play or getaway, or perhaps embrace the season with fall activities.

Connecticut is filled with rich history, which often means a rich haunted history. Dare to visit the Mark Twain House, said to be haunted by the “lady in white” or the Lockwood-Mathews Mansion Museum, where you may encounter the spirits of Legrand and Florence Mathews. Brave the haunted history of Historic Mystic Country or visit these (potentially) haunted cemeteries. If you look closely, you’ll find there’s plenty of places to ghost hunt in every region of Connecticut – a thrilling way to spend this extra day of play.

Christmas Long Weekend

With Christmas on a Friday, a three-day holiday weekend will likely put you in the spirit for a holly jolly getaway or other merry outings.

Stay overnight in the heart of historic Old Wethersfield at the Chester Bulkley House B&B located right near Heirloom Market, the festive filming location of the Lifetime movie, “Rediscovering Christmas” and the Hallmark movie, “Christmas on Honeysuckle Lane.”  While you’re there, take advantage of Heirloom Market for its farm-to-table goods and stop for a bite with a view at River – A Waterfront Restaurant & Bar.

To get even closer to the holiday magic, take an overnight at the Griswold Inn, which is known for its year-round Christmas tree and was the actual filming location of Hallmark movie, “Christmas at Pemberly Manor.” While you’re there, take a ride on the Essex Steam Train’s annual North Pole Express, and enjoy an on-board performance of The Night Before Christmas while wearing your pajamas.

For great a day trip activity over your long weekend, try these winter experiences you just can’t have in the city. Visit one of Connecticut’s most picturesque Christmas sights, the West Cornwall Bridge and at night, see the stunning holiday lights at Lake Compounce in Bristol. For a winter culinary adventure, try these festive winter restaurants from rooftop igloos to “après-ski” inspired pop-up bars.

New Year’s Long Weekend

Since New Year’s Day is on a Friday, your New Year’s Eve leads right into one last three-day weekend - what better way to ring in the new year?

If you’re looking for a quiet and cozy New Year’s weekend, Connecticut inns and B&Bs like the Copper Beech Inn in Ivoryton, the Daniel Rust House in Coventry, or the Inn at Woodstock Hill in Woodstock are your go-to places. You may even choose an inn with a stunning spa like the Mayflower Inn & Spa in Washington. For a cozy stay but an active outing, stay at Old Riverton Inn and spend your weekend skiing and snowboarding on the sixteen trails of Ski Sundown in New Hartford.

If New Year’s to you means raising a glass and starting the party, consider a weekend at one of Connecticut’s casinos.  At Foxwoods Resort Casino play the 3,400 slot machines and more than 250 table games, go bowling at High Rollers Luxury Lanes & Lounge, shop at the Tanger Outlets or dance the night away at Shrine Nightclub. At Mohegan Sun enjoy 47 restaurants, bars and lounges; three entertainment venues and 130,000 square feet of upscale shopping, and over 5,000 slot machines and 300 table games, including 33 poker rooms. Catch a show at Mohegan Sun Arena or put on your dancing shoes at Vista or Avalon Nightclub.

Classic Long Weekends

Finally, don’t forget the classic holiday weekends we look forward to every year – each just as worthy of a delightful getaway.

For Memorial Day weekend, take a lighthouse tour getaway or take advantage of the spring weather and stroll walkable town centers.

Spend Labor Day weekend discovering all the fun to be had at Connecticut waterfalls or soak up the last bit of summer with this summer getaway.

For Columbus Day weekend, plan the perfect fall foliage road trip or try these romantic fall getaways.

For Veteran’s Day weekend, make an adventure of the Connecticut Wine Trail with this Litchfield Hills getaway or stay a night (or two) somewhere you can cozy up by the fire.