Two hands held together to make a heart.

There are plenty of reasons to love February in Bennington — 29 of them in 2020! The sweetest reason of all is Valentine’s Day, which celebrates love in all its many forms. If you are fortunate enough to be in Bennington for Valentine’s Day, check out some of these great ideas to celebrate the season of love…

Make Your Own Valentine 

A homemade Valentine with LED lights
Make your own Valentine! Photo credit: Bennington Area Makers

We’ve got a few great make-your-own-Valentine workshops in February, for both kids and adults. If you want to say “I love you” with a creation of your own design, you can do it in downtown Bennington!

  • Make your own Valentine at Beyond Gallery and Gift Shop – This special craft event will coincide with the opening of the new group show, “Portraits.” The workshop space will include everything you need to make one-of-a-kind cards. This is a free event that is open to all ages. Drinks and snacks will be available. Friday, February 7, 5 – 8 pm at the Beyond Gallery and Gift Shop on Main Street. 
  • Make your own electronic Valentines – Two workshops, one geared toward youth and one toward adults who want to create their own light-up Valentines for someone special. The youth workshop is Saturday, February 8, 10 am – 12 pm at Bennington Area Makerspace.  Children must be accompanied by an adult. The adult workshop will take place on Wednesday, February 12, 5:30 – 8 pm. 239 Main Street, Bennington.

Say ‘I Love You’ While Shopping Local

What’s the best way to spread the love on Valentine’s Day? How about giving your favorite Valentine a unique gift from one of our fabulous downtown shops? While there are all kinds of cool gifts available downtown, you know you can’t go wrong with chocolate and flowers. These local shops will be more than happy to help you kick up the romance.

The Gift Garden

A colorful flower arrangement created by the Gift Garden in Bennington, VT for Valentine's Day
Just one of the beautiful flower arrangement designs available at the Gift Garden. Photo credit: The Gift Garden

Located on Main Street in downtown Bennington, the Gift Garden has been proudly serving the local community since 1976. They specialize in providing fresh flowers for all occasions and are happy to deliver locally. Roses are probably the top choice for Valentine’s Day flower arrangements, but you can also view a unique selection of modern and classic arrangements on their website. Stop into the Gift Garden to browse special Valentine’s Day gifts — the perfect accompaniment to any flower arrangement. 

The Village Chocolate Shoppe

Chocolate covered strawberries! Photo credit: The Village Chocolate Shoppe

There’s just something about sharing a few pieces of decadent chocolate with the one you love. At the Village Chocolate Shoppe on Main Street in Bennington, you can create your own chocolate gift box with your Valentine’s favorite flavors, including decadent homemade fudge, beautiful truffles, and cream-filled delicacies. If you really want to impress, place an order for the most indulgent chocolate-covered strawberries, which will be available for pick up on February 13th and 14th. 

The Tuscan Sunflower

Just one of the many floral designs you can find at the Tuscan Sunflower. Photo credit: The Tuscan Sunflower

The Tuscan Sunflower is a local, full-service flower shop on North Street that specializes in an extensive collection of cut flowers and tropical plants. Stop in to place your unique Valentine’s Day flower arrangement for your sweetie, or pick up a unique gift that you won’t find anywhere else. Special Valentine’s Day gifts include plush animals, holiday-themed balloons, and locally-crafted chocolates.

Indulge in Local Culinary Creations

One of the best ways to share a little romance with the one you love is to get out of the kitchen for a night on the town.  Bennington is fortunate to have some deliciously romantic restaurants where you can feed both body and soul. Here are some recommendations for a romantic Valentine’s Day meal in Bennington. Reservations are recommended.

Miller’s Toll Dinner Club and Lounge

A snazzy cocktail at Miller's Toll in Bennington, VT
Photo credit: Miller’s Toll

With its ambient lighting, private dining rooms, and delectable cocktails, The Miller’s Toll is a great spot to cozy up for a romantic evening. The small plates and finger foods on the provisions menu are perfect for sharing with someone special, and for Valentine’s Day, Miller’s Toll will be offering chocolate-themed specials that will put you in the mood for some good lovin’! 

The Grille at Mt. Anthony Country Club

For the most romantic and intimate atmosphere, you can’t beat the fireside dining at Mt. Anthony Country Club. Casual menu selections feature the finest local ingredients, from decadent comfort food to luscious steak and seafood entrees. A special Valentine’s Day menu will feature classics like seafood bisque, Surf & Turf, homemade ravioli, and much more. Bring your appetite and settle next to the fireplace to celebrate good food with the one you love.

Photo credit: Greg Nesbit

Allegro Ristorante

Photo credit: Allegro Ristorante

Focusing on eclectic Italian cuisine in a most inviting setting, Allegro Ristorante has been dishing up superior meals since 2007. A Valentine’s Day meal at Allegro is sure to give you all the feels. Choose a glass or bottle from their extensive wine list, and order up a plate of pasta to share Lady-and-the-Tramp style. Finish your meal with something sweet — the rotating dessert selection is always on point!


At Pangaea, you’ve got two distinct dining styles in one beautifully decorated restaurant. For casual dining and cocktails, cozy up in the Lounge. For a more refined menu, make reservations at Pangaea, where you’ll be treated to formal fine dining with selections elegantly prepared from local ingredients. A special Valentine’s Day menu will be offered from 2/13-2/15 and will include two courses for $30 or three courses for $38, and a wine pairing for $10. Choose from delicacies like Scotch butter shrimp, Faroe Island salmon, or pan-seared diver scallops. Whether you choose formal or casual for your Valentine’s Day feast, you’ll love the elegant style and delicious food available at Pangaea and the Lounge.

Dessert at Pangaea in North Bennington, VT
Photo credit: Pangaea

The Publyk House

A romantic dining table set for two at the Publyk House in Bennington, VT
Photo credit: The Publyk House

Dinner with a view? Don’t mind if we do! Start your night at the Publyk House in the cozy dining room with a special Valentine’s Day menu and a great selection of beer, wine, and spirits. Look out on Mt. Anthony with the one you love and thank your lucky stars that you get to be in Bennington on Valentine’s Day! Specials include a variety of starters, soups, entrees, and desserts that you won’t want to miss, including a special Valentine seafood platter, grilled filet mignon, and the most decadent molten chocolate lava cake. 

Spice up Your Night with These Local Events

Of course, there’s more to Valentine’s Day than flowers and food. For a little something extra, head into downtown Bennington for a night of excitement.

Gypsy Layne at Oldcastle Theatre

Gypsy Lane Cabaret at Vermont Arts Exchange in Bennington, Vermont
Photo credit: Vermont Arts Exchange

For two nights only, February 14 and 15 at 8 pm, head to Oldcastle Theatre for a sizzling show with Gypsy Layne Cabaret and Company. Named after the pioneer of burlesque, Gypsy Rose Lee, Gypsy Layne is dedicated to self-acceptance, body positivity and inclusivity. Hailed as “a sexy highpoint of classic burlesque entertainment in the Berkshires” by Berkshire magazine, Gypsy Layne’s hallmark of bawdy humor, live singing, dynamic dance routines, and cheeky sex appeal are prominently featured in their sizzling shows. Mature audiences only. Tickets: Advance $22, At-the-door $27

Dinner and Dancing at the Dutchman’s Tavern

Looking to dance the night away? The Dutchman’s Tavern will be hosting a romantic Valentine’s Day dance party featuring Sawyer Country and some good old country tunes. 8 – 11 pm. 

Looking for more ideas to celebrate Valentine’s Day? Check out Bennington’s complete listing of local shops and restaurants.