romantic gift ideas_cloud 9 livingYour chance to deliver (and delight in) the very best Sweetest Day ideas is right around the corner! As the third Saturday of October scoots closer on the ol’ calendar, it’s time to start thinking of ways to celebrate and really ‘wow’ those special someones in your life!

Yes, “someones” — meaning your affectionate efforts don’t have to be geared towards just one person. In fact, Sweetest Day gifts or activities don’t necessarily even have to be romantic, either. (But pump those brakes before your brain takes those remarks in a weird direction!) Because truth be told, the holiday’s roots are not originally founded in the notion of being cute ‘n’ coupled up. (Say what?!)


Then, what is the origin of Sweetest Day? So glad you asked! Sweetest Day’s history actually lies in October of 1922, when a cohort of volunteers, led by a kind-hearted confectioner named Herbert Birch Kingston, passed out over 20,000 boxes of candy to forgotten populations in the Cleveland, Ohio area… the poor, orphans, shut-ins, newsboys…

If you’re looking to go beyond gifts to celebrate this charming holiday, here are some downright great things to do for Sweetest Day to get some plans penciled in — whether with family, friends, a significant other, or even strangers needing some TLC!


17 Unique Sweetest Day Ideas Worthy of Warming Hearts


1. Make sweet treats together.

Making candy sure beats buying it in a box. And it gives you a fun Sweetest Day activity to enjoy together. Check out a local cake decorating or chocolate-making class. Or do something fun and easy at home, like dipping and decorating pretzel rods or candied apples.

cute ideas for Sweetest Day


2. ‘Tis the season for alma mater games!

Reunite with old friends by visiting your college stomping grounds together. Use the third weekend of October to relive the glory days and enjoy some top-notch tailgating. And if you’re in a relationship, this is a fun way to invite your main squeeze along to discover some fun insights to a past chapter of your life.

Sweetest Day weekend activities


3. Bedazzle your Sweetest Day with bling.

Jewelry is a classic gift for holidays like this. There’s no harm in using your October Saturday as an excuse to buy a boyfriend, girlfriend, or best friend a trendy yet meaningful accessory. And if you prefer, you can always flex your DIY muscles and make your own jewelry. A local craft-specialty spot (preferably with cocktails) is a fun place to spend time with a special someone or group of friends!

fun Sweetest Day ideas with friends


4. Take a haunted city tour.

October is the prime time for spooky festivities, so this Sweetest Day idea is no exception! If you’re looking for something a bit less mainstream or commercial-y than the typical haunted house, check out local ghost tours. Adult beverages are usually available for purchase as you make your way to various venues. So grab a cold one and delight in an evening of spine-tingling tall tales as a couple or a crew of friends.

unique Sweetest Day ideas


5. Sample wine or craft beer together.

Sometimes, nothing says “love” or “you’re my best bud” like sipping your way through local breweries. There’s no cozier way to kick back on a crisp, fall afternoon than with good company and tasty hops. Especially during the return of pumpkin ale season! Of course, vineyard tours work, too, if that’s more your samplin’ speed.

meaning of Sweetest Day


6. Leave “love/like ya” notes around.

This is one of the easiest yet gesture-packed things to do for Sweetest Day. And it’s versatile enough to share with any number of recipients: a friend, coworker, significant other, parent, etc. A couple meaningful words can make for one happy heart. So jot down a few compliments or words of encouragement, then cleverly stash them around to be found.

Sweetest Day history


7. Get your country on!

Whether you’re the ultimate country fan, just dabble, or claim not to touch the stuff — a night like this is guaranteed to have you smiling as you kick some dust up together! Start with a hearty, Southern dinner at a spot like LongHorn Steakhouse, Texas Roadhouse, Cracker Barrel or the like. Then top the evening off at a line-dancing hot spot. Plaid, denim and boots are highly encouraged to bring the best out of this Sweetest Day idea.

Sweetest Day ideas for boyfriend


8. Pack a picnic ‘n’ park hamper.

Enjoy a delightful afternoon outside. Load up your basket with tasty apps or sandwiches, a classy bottle of wine, and fun entertainment (think along the lines of a deck of cards, Frisbee, crosswords or kite). Feel young at heart kicking back with your favorite person or group of pals, basking in fresh air.

who is Sweetest Day for


9. Lay street-sweetness on strangers.

Brighten up Sweetest Day for men and women who may be experiencing some dark times. Buy candy or whip up baked goods. Then use mail labels to create some personalized stickers to add encouraging notes (like “you are loved” or “have a sweet day,” etc.). Pop those gems on your tasty treats, then hit safe city streets to pass them out. You can also donate them to a shelter to be distributed, but if that’s the route you take, be sure to only buy wrapped candy (for health/screening purposes).

gifts for Sweetest Day


10. Go fall camping.

Whether you’re looking for a romantic weekend getaway, or a colorful change of scenery with friends or family — this Sweetest Day idea is a wonderful way to go! Escape the pace of ‘normal life.’ Enjoy quality time with those you hold near and dear, with fewer distractions. Admire Mother Nature’s artistry as you delight in the great outdoors.

Sweetest Day ideas for girlfriend


11. Do a potluck.

This is a great way for a group of any size to savor some Q.T. together. Especially when few will ever complain about a reason to mow down some seriously sensational eats. Let alone great company. And if you’re a couple, you can make it into an easy two-part “surprise potluck”: one of you does the dinner itself, the other does drinks and dessert.

Sweetest Day ideas for friends


12. Snag your seasonal pumpkins.

The best Sweetest day gifts are those activities that keep on giving. This is the perfect weekend to venture out to the patch to soak up some fall fun, and find your prize gourd. It’s just close enough to Halloween to think creative carving thoughts, with a bit of time to spare. Once you have a winner, delight in a carving night, and add even more fun pumpkin activities to the mix!

romantic Sweetest Day ideas


13. Get in on autumn activities!

Fall brings no shortage of finding fun events that double as great Sweetest Day ideas. Enjoy the annual festivities that often accompany the autumn season. Go apple picking. Get lost in a corn maze. Devour delicious homemade donuts and cider. Check out art shows and live music. Try your hand at a few cute DIY fall crafts. Indulge in pumpkin-flavored everything.  And plenty more!

best Sweetest Day ideas


14. Sail away on a picturesque bay.

If you’re lucky enough to live in a tolerable climate this time of year (or have a strong ‘layering’ game), then this is a great Sweetest day idea for a boyfriend, girlfriend, or group of friends. Savor the crisp air of the season with a scenic cruise, complete with spectacular views. Nothing beats the adventure and ambiance of a boat ride on the SF Bay, NYC Harbor, Chicago shoreline, and other stunning destinations.

what to get a guy for Sweetest Day


15. Cozy up to a campfire.

Whether it’s in the rugged wilderness, or around a fire pit in the comfort of a backyard — this Sweetest Day idea is always a crowd-pleaser. And it lives up to that claim to fame regardless of whether the “crowd” comes as just you two, or a whole slew of you! So crack a cold one or pour a swanky glass of wine. Bust out the s’more supplies. And relax around those dazzling, dancing flames.

fun ideas for Sweetest Day


16. Pamper as a pair.

There’s no better time than Sweetest Day to pump the ‘daily life’ brakes a bit and unwind. So sweep an S.O. off his/her feet with a couple’s massage. Or kidnap a best bud for some exquisite mani-pedi action to celebrate your friendship in ahhh-mazing style. And don’t forget — it’s wonderful to show yourself how much you care, too… So if you need to treat yourself to some solid “me time” at the spa, do it!

great Sweetest Day ideas for her


17. Visit someone who may have no one.

For some, any holiday can be a tough reminder of the solitary life. As such, one of the most beautiful Sweetest Day ideas on Earth is to share the occasion with someone who may be alone. Volunteer with friends, family or your main squeeze. Head to a senior living center, shelter, soup kitchen, or similar spot that may house some folks flying solo. Spend the day serving others, swapping stories, making new friends, and exemplifying the true roots of Sweetest Day! It’s guaranteed to do the heart extra-good — for all parties involved.

origins of Sweetest Day