A Busy Chocolate Season Ahead – Fall Fairs and Festivals
Dean's Sweets little chocolate pumpkins

A Busy Chocolate Season Ahead – Fall Fairs and Festivals

When the temperatures start to cool, we know we’re headed toward a busy chocolate season. And there’s nothing we like more than a good fall fair. We’ve got several coming up in Maine and in the Northeast, so maybe we can tempt you to come out and find us. Plus, we’ll share a sneak peek at some early holiday shows and boutiques.

Dean's Sweets Maine sea salt caramel sauce

Freeport Fall Festival | Freeport, Maine

Fri – Sun, Oct 6-8

You will find us right outside the L.L.Bean flagship store. We’ll be sampling our Maine sea salt caramel sauce, hot fudge sauce, and who knows what else. We’ll have plenty of little chocolate pumpkins, cocoa bombs, and truffles, of course. This is our first time at this fair and we hear it’s a great one. There will be over a hundred vendors and a lot of great Maine goods to keep you going this fall. Find out more here.

New York Sheep & Wool Festival | Rhinebeck, NY

Sat – Sun, Oct 21-22

Are you a knitter? Or possibly a spinner? If you are, you’ve definitely heard of the NY Sheep & Wool Festival. It’s a real mecca for anyone in the fiber arts community. I realize it may seem out of place for us to be involved in this fair, given we don’t sell yarn. But here’s a major insider tip: there’s a whole building devoted to gourmet food. Many of the vendors are local to the Finger Lakes region of New York, representing small, high-quality vineyards. If the chocolate (and the yarn) doesn’t tempt you, maybe the free samples from the wineries will. Rhinebeck itself is a super fun little getaway too, with a great restaurant scene. Come find us! Find out more here.

Dean's Sweets chocolate pumpkins and Jack O' Lanterns

East Bayside Halloween Fest | Portland, ME

Sat, Oct 28

Stroll around Portland’s East Bayside for a fun day with the family or an excursion with your best buds. It’s like and open house and a pub crawl all rolled in one. Try something yummy and rummy at Three of Strong or enjoy the creative space at Taproot Market, where you’ll see exquisite hand-made goods by crafters from all around Maine. Come for the chocolate or the beer, with or without a costume, and while you’re at it, donate clothing and household items at the Goodfire Brewing tasting room where $1 from all full-size drafts will go directly to Maine Needs. You’ll be doing good while having fun. And no one can blame you if you go for a second Goodfire draft either. Find out more here.

New England Christmas Festival | Monhegan Sun, CT

Fri – Sun, Nov 3-5

Yes, Christmas! Voted the best craft festival in New England, here’s a very early holiday fair that has attracted thousands of devoted shoppers from all over New England for many years. It used to be called the Boston Christmas Festival when, for decades, it was in the old Boston Seaport building. Now it’s even bigger, and parking is MUCH easier. (If you go to the website, you can get $2 off the admission fee.) It’s a fun trip for a girls’ weekend or some time away with a special someone. Shopping by day, Casino by night. Yes, it’s all that plus a spirited holiday vibe (think red, white, and green sequins and penguin motifs) that everyone takes seriously in the least serious kind of way. Find out more here.

Dean's Sweets chocolate turkeys

St John’s Holiday Boutique

Sat, Nov 18 | Hingham, MA

There will be chocolate turkeys for Thanksgiving, Hanukkah gelt for the kids, and holiday assortments to last throughout the season. Hanukkah starts early this year (Dec 8!) so it’s not too early to shop. Plus there are many other high-quality vendors at this curated boutique so you can get serious about your holiday needs. Find out more here.

Wellesley Hills Marketplace

Sat, Nov 18 | Wellesley, MA

A favorite holiday shopping event with over 200 artisans and vendors from all over New England. In addition to chocolate, you’ll find handmade jewelry, clothing, and artwork. There are tickets on sale now and even an early-bird exclusive shopping option if you want to get there before all the good stuff is gone. Find something for everyone on your list, and definitely find something for yourself! Find out more here.

Church of the Redeemer Christmas Market

Fri – Sat, Dec 1-2 | Chestnut Hill, MA

A hidden gem of a market in a beautiful church in Chestnut Hill, MA. Walk through the Christmas tree garden just for the wonderful scent of the dark spruces and wreaths. Vendors offer an array of jewelry, hand-carved toys, stationary, home goods, clothing for men and women, and of course, your favorite, chocolate! It’s a quiet, no hassle, steeped-in-history shopping experience that is far, far from the mall. It’s a favorite of ours to be in a warm and welcoming place. We hope you’ll find us there! Find out more here.

Dean's Sweets peppermint truffles

Merry Madness!

Sat, Dec 9 | Portland, ME

A magical winter shopping crawl around the heart of Portland. Walk through the downtown and Old Port areas and find treasure and treats at many of the locally owned business. Stores will stay open late that night for maximum fun. And many stores will offer samples or a taste of something holiday-ish to keep you nourished while you shop. There’s a before-party too, with raffles and giveaways and lots of holiday cheer. Year after year, this is a sold-out event, so get your tickets soon. It’s one of those events not to be missed! Find out more here.

It will be a very busy fall fair and winter festival season ahead, with more events surely to be added to the schedule (stay tuned!). Come out for the lights, come out for the music, come out for the chocolate and caramels and confectins. Plan a scrumptious dinner ahead in the amazing Portland foodie scene. And plan a nightcap at the end in a snug little pub. It’s a busy, fun, happening time with so much going on! We might not sleep much this time of year, but we honestly love it. Chocolate season is every season, and this fall offers the best of the best.