Valentine’s Day in Litchfield: Take Romance Beyond the Obvious

Valentines Day in Litchfield, Milkhouse Chocolates
Milk House Chocolates

Flowers, chocolate, wine, and a dinner at a fine restaurant. These are the classic ingredients for Valentine’s Day romance, and they’re classic because they deliver on their promise year after year.

Litchfield has you covered on all fronts in fine style. See our Visit Litchfield CT Shopping page for the flowers, our Chocolate & Ice Cream page for the chocolates, and the Gourmet Shops & Provisions page for the wine and more.

To book dinner at a fine restaurant, head to our Restaurants page and follow the quick and easy links to social media pages where Valentine’s Day menus are being posted.

This post is aimed more at non-traditionalists and those who resist the implied directive to celebrate the official holiday of love on a weeknight because that’s where the date chosen by a pope falls most years.

(The last time Valentine’s Day fell on a Saturday was 2015 and that won’t happen again until 2026, and as for the pope, it was Pope Gelasius I who established the Feast of Saint Valentine in AD 496 and tethered it to Feb. 14.)

Before digging in, a caveat: Take loved ones out for dinner on Feb. 14 if you can. Our restaurants just brought home a whole bunch of top dining awards, regionally and statewide, and they work up pretty magical Valentine’s Day menus.

Whether or not you go out, here are five recommendations for V-Day romance with a twist—we’re thinking Saturday or Sunday, or even Tuesday during the day when it will be 55 degrees—followed by a sampling of related special events.

  • Walk in the Woods
    Miss Edith’s cottage at Topsmead in the summer.

    We think it’s the most romantic thing you can do in Litchfield. White Memorial is an obvious choice for a venue, and Topsmead State Forest, with its English-style cottage, exudes romance. Wherever you walk (check our Outdoors page for more resources), pair it with pitstops at bakeries and coffee shops and perhaps lunch, too.

  • Shopping Surprise

    Come to Litchfield with your sweetheart and explore the shops that most appeal to your special someone. That’s romantic enough, but we suggest sealing the deal by observing what your date loves the most and then creating whatever subterfuge necessary to secretly buy that item and present it as a V-Day gift during cozy time at home that evening.

  • Sweet Litchfield Tour

    Start with a sweet breakfast one of our scratch bakeries; we’re thinking of cinnamon buns, muffins, scones and more + fine coffee or tea. While you’re in town, visit the old-fashioned Litchfield Candy Company, and then take a drive north on Route 63 to experience Milk House Chocolates at Thorncrest Farm.

  • Haight-Brown Vineyard

    Valentine's Day, Haight-Brown VineyardThe invite on the website of Connecticut’s oldest farm winery is a Valentine in itself: Visit our bar room for wine and cocktail flights, wine, cocktails and beers by the glass, wines by the bottle. Order crab cakes, short rib sliders or our famous house charcuterie from our Café menu! Head outside to our deck and enjoy picturesque views of the vineyard! In the winter, cozy up by the fire with a mug of warm spiced wine! See the website to connect.


  • Litchfield Distillery Visit

    Valentine's Day, Litchfield DistilleryLitchfield Distillery offers complimentary tours and sample tastings of its award-winning spirits, arranged by reservation on the website. Walk-ins are also welcomed if a timeslot isn’t full. Tours are offered on the hour (Mon-Sun) beginning at 11 a.m. The last tour begins at 4 p.m. (except Sunday when the last tour begins at 3 p.m.). See the website for details and the link to reserve. For questions, call us at 860-361-6503. Visit the Facebook page for updates. Oh, you’re wondering why a distillery tour and tasting is romantic. Consider the tasting notes on the Double Gold Medal-winning Straight Bourbon Whiskey:
    Nose: Hints of vanilla and butterscotch are complemented by a nice balance of apple, cinnamon, and baking bread.
    Palate: Spicy and a little sweet with nice notes of rich tobacco and toasted baking spice; a hint of apple.
    Finish: Full mouthfeel with heat in the back palate. Extremely long, spicy finish with a hint of citrus.

Valentine’s Day Events

  • The Love in Litchfield Lantern Tour

    As of Wednesday morning (Feb. 8) it appeared that spots were still available but act fast as the tour will sell out. The special Valentine’s Day “lantern” tour of Litchfield’s Historic District takes place Friday, Feb. 10 at 5:30 and features the great love stories of Litchfield’s past! The tour starts at the Litchfield History Museum (7 South Street) where guests will enjoy historically inspired cocktails and treats before grabbing lanterns and heading out on our tour. The cost is $15 for LHS Members and $20 for non-Members. Details and registration are online.

  • Victorian Valentine’s Day Workshop

    The Litchfield Historical Society’s annual Family Victorian Valentine Workshop takes place Saturday, Feb. 11, from 10 a.m. to noon at the Litchfield History Museum (7 South Street) Valentine’s Day in the Victorian era was an elaborate affair. Adults and children alike can draw inspiration for the Society’s collection of Victorian and early 20th century valentines while learning traditional papercrafts and making their own cards for family and friends. Tea and cookies will be served.   The Victorian Valentine Workshop is $10 for members, $15 for non-members, or $30 for a family. Register Online Here
  • 21st Annual Bob and Peg Andrulis Memorial Sweetheart Run/Walk

    We’ll admit that a 5-mile run or 3-mile walk isn’t everyone’s idea of a perfect Valentine’s Day warmup, but for others it’s just the ticket. This USATF-certified course starts and finishes at the Litchfield Community Center, which benefits from the proceeds. Pre-registration is $30, $10 for children (10 & under) and free for those 80 and older ($35 after 2/9/23 and on the day of race. Long sleeve T-shirts go to the first 150 registrants, and there will be goodie bags and refreshments. To pre-register online, go to online registration and to register with application form go to paper application form. Registration day of event 9:00 a.m. – 10:45 a.m.

  • Singles Mingle

    The Litchfield Community Center’s first-ever Singles Mingle, for those 245 and older, is exactly what it sounds like, an invitation to find love or friendship event. Swing by to play games, speed date, and get to know other singles in your area. Feel Free to BYOB. Pre-registration is required and can be completed online.

  • Ducks in Love

    The Ripley Waterfowl Conservancy’s “Ducks in Love” weekend features a tour of the world-class aviaries with an Aviculturist and opportunities to observe waterfowl in their brilliant breeding plumage, and perhaps courtship displays. Afterward, cozy up by the fire with a warm cup of spiced cider. Saturday, Feb. 18, is the general Ducks in Love tour and refreshments. For a more private experience (and a box of Thorncrest Farm chocolates), book a guided tour on Sunday Feb. 19. To sign-up and for more information, visit the “Ducks in Love” page: