Valentine’s Day Date Ideas

With Valentine’s Day a week away and on a Wednesday, now is the time to plan some date night fun if you haven’t already. I’m sure that if you’re going away or doing something elaborate, you’ve already solidified your plans. Right? My boyfriend and I had started our planning on January 2nd since we’re celebrating Valentine’s Day and our one year anniversary. During the process, I found a lot of inspiration for some date ideas for Valentine’s Day or just any time this winter (you can check out some more winter date ideas here).

Just as a note, I’ve focused a lot of my ideas for Connecticut and part of the surrounding Northeast/New England region (Massachusetts, New Hampshire, Vermont, Maine, Rhode Island, and New York).

For Those With a Sweet Tooth

If you and your SO have a wicked sweet tooth, consider going on a tour of one of New England’s many ice cream and chocolate factories! You may even want to sign up for a tasting event instead. Make it a day of trying all of the chocolate and sweets you can!

Connecticut Chocolate Trail, Statewide– If you’re looking for an all day experience, take your pick of locations along the Connecticut Chocolate Trail. Some of the recommended stops include Bridgewater Chocolate Factory (Brookfield and West Hartford), Chocolate Shell (Old Lyme), Divine Treasures (Manchester), and Isabelle et Vincent (Fairfield). You can see more stops here.

Ben & Jerry’s Factory Tour, Vermont– See how all of your favorite flavors are made then then get to enjoy them and try some new ones! Tours are available seven days a week, from 10am-6pm. Tour costs $4. You can find out more here.

Taza Chocolate Factory Tour, Massachusetts– Love fancier chocolates? Learn about Taza’s stone ground chocolate and get to try some out. Tours last 45 minutes, with it partially being a sit down presentation to start off. Tours cost $8 and have to be booked online, ahead of time. You can learn more here.

For the Wanderers

If you’re looking for a weekend away to celebrate your love, take a look at some of these mini-adventures.

Winter Hiking– No matter what state you live in, there are plenty of trails that you can hit for a day. Take in the snowy sights, challenge yourselves, and pack a thermos of your favorite hot drink! Just note that you should always be more prepared for winter hiking than you would be doing the same trail in the summer. What might be an easy climb during the rest of the year could be dangerous when covered in snow and ice. If this does seem like something that you’re interested in, here are some suggestions below:

  • Connecticut: Devil’s Hopyard State Park in East Haddam; Rugged Mountain in Berlin; Steep Rock Preserve in Washington Depot; Bluff Point in Groton.
  • Massachusetts: World’s End in Hingham; Borderlands State Park in North Easton; Myles Standish State Forest; Mohawk Trail State Forest in Charlemont.
  • New Hampshire: Lincoln Woods in Lincoln; Diana’s Baths in North Conway; Canon Mountain in Franconia; Mount Mondnock in Jaffery;
  • Vermont: Elmore Mountain; Hubbard Park in Montpelier; Robert Frost Trail in Ripton; Owl’s Head in Groton; Molly Stark State Park;
  • Maine: Witch Hole Loop at Arcadia National Park; Forest City Trail in Portland; Camden Hills State Park.
  • New York: Silver Mine Lake Trail; Bear Mountain State Park; Whiteface Mountain.

And for safety, here are some tips from Northeast Mountaineering:

  • Always check the forecast; the weather changes by the minute in the White Mountains.
  • Go with a friend who has done some winter hiking before.
  • Test your layers on non-committing terrain. Even around town or on a local trail system.
  • Have bail out plans.
  • Let someone know where you are going and what trails you intend to use.
  • Take zero risks. Turn around if you need to!
  • Have Fun!


For the Snow Bunnies

Love hitting the slopes? The Northeast has a lot of options for those who want to spend some time mountainside before cuddling up in front of a fire. Just as a note, if I got into all of the ski areas around New England, this already long post would be even longer. Make sure to take a look at what is offered near you!

Powder Ridge Park in Middlefield, CT– This ski resort was named one of the best in Connecticut. Like a few of the ski areas on this list, they have a little something for everyone. Like skiing, they’ve got you covered. Want to go tubing instead? They have that! They even have snowbiking available on site! You can find out more about Powder Ridge here.

Other Connecticut Ski Areas: Ski Sundown in New Hartford; Mount Southington in Plantsville; and Woodbury Ski Area in Woodbury.

Jiminy Peak in Hancock, MAJiminy is another ski area rated one of the best in its state. When you go there, it borders on feeling like a European Ski Village, although it doesn’t really look like it. If you’re looking for some great slopes followed by an evening of music and drinks, this may be a good option for you.

Other Massachusetts Ski Areas: Ski Butternut in Great Barrington; Wachusett Mountain in Princeton; and Nashoba Valley in Westford.

Cranmore Mountain in North Conway, NH– New Hampshire is home to some of the best skiing around and Cranmore is no exception. They offer lots to do for both the skiier and winter adventurer. Not to mention that it is nestled in a great little village. This one is definitely my favorite skiing and tubing get away!

Other New Hampshire Ski Areas: Loon Mountain in Lincoln; Bretton Woods in Bretton Woods; Wildcat Mountain in Gorham; and Cannon Mountain in Franconia; and more!

Okemo Mountain Resort in Ludlow, VT– See, New England has tons of top rated ski resorts. Okemo is great because, again, these is plenty of do for all visitors. Not to mention they have plenty of events going on. Planning on heading up for Valentine’s Day? They have a special scavenger hunt for couples on the trails! Not to mention torchlight parades and fireworks throughout the winter!

Other Vermonth Ski Areas: Stowe Mountain Resort in Stowe; Mount Snow in Dover; Sugarbush in Warren; Killington Ski Resort in Killington; and more!

For the Beer Lovers

Love beer? Are you and your lover beer snobs? Or, at the very least, just really into beer. Look no further than your own back yard for the chance to tour some breweries or just relax with a nice pint.

Allagash in Porland, ME– Looking to try out some beer and see how it is made. Allagash offers free tours and the option of a grand tour if you’re interested. Make sure to check their website to see what’s in the tasting room that day.

Thomas Hooker in Bloomfield, CT– This small brewery is great if you’re looking for a bit of local flavor. Drop in for a Friday Open House or tours on Saturday afternoons. Tours do cost $5. Find out more here.

Harpoon in Boston, MA and Windsor, VT– Harpoon gives you two options for visits. Their larger brewery in Boston offers tours for $5 and some delicious pretzels while you wait along with a wide selection of their beers.  The Windsor location also offers tours for $5 and has a fantastic restaurant inside. Plus, it it located in a little compound with all sorts of interesting things to look at.


Of course, there are thousands of other ideas to consider this Valentine’s Day. The important part is doing something together, even if it’s just making dinner together at home and watching your favorite movie or show. Enjoy your time together! If you’re going to plan a date: good luck and happy planning!


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