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Massachusetts is a wonderful spot to spend Valentine’s Day for residents and visitors alike. From the fine dining and historic spots in Boston, to the scenic views of the Berkshires and the Cape and everything in-between, there are tons of events and attractions across the state to consider taking your special someone.
GREATER BOSTON | NORTH OF BOSTON | SOUTH OF BOSTON | CAPE COD & THE ISLANDS | CENTRAL MASSACHUSETTS | WESTERN MASSACHUSETTS
Greater Boston
If you’re looking for a date night in Boston, you’ve got options. For food lovers, try the fine dining of the North End. The Museum of Fine Arts, the Isabella Stewart Gardner Museum, the Institute of Contemporary Art, and the MassArt Museum are perfect picks for art aficionados. Or if your date enjoys the outdoors, try taking a walk around the Boston Common or the Back Bay Fens. Finally, don’t miss the one-of-a-kind views of View Boston within the Prudential Center.
Greater Boston Events
Boston, Recurring Daily
Witness a dazzling display of lights, the Tunnel of Love, at Christopher Columbus Park during the month of February.
Throughout Boston, February
Step into an evening of unparalleled elegance and indulgence at our Grand Dinners in the iconic Wharf Room. With sweeping harbor views as your backdrop and a setting steeped in timeless grandeur, these evenings promise to be nothing short of extraordinary. Imagine a night where exquisite wines and decadent cuisine come together in a symphony of flavor, expertly curated by world-renowned winemakers and our celebrated chefs.
Friday Night Date Nights at The Bosworth
The Bosworth, Boston, Recurring Weekly on Friday
Make Friday evenings something to look forward to with our Friday Night Date Night Prix Fixe—perfect for a night out with your loved one, someone special, or even a girls or guys night! Enjoy a thoughtfully crafted menu featuring the season’s finest flavors, with the option to enhance your meal with perfectly paired wines. Whether it’s a planned evening or a spontaneous outing, Friday nights are made for sharing great food, great wine, and great company.
Couples’ Chocolate Truffle Making Class
Boston Public Market, February 8
Join us at the Boston Public Market for a sweet and romantic experience. Learn how to make delicious chocolate truffles with your significant other in a fun and interactive setting. This hands-on class will teach you the art of crafting decadent treats that you can enjoy together or give as gifts. Don’t miss out on this special event filled with love, laughter, and of course, chocolate!
Valentine’s Day Cocktail Class
Rosa Mexicano, Boston, February 13
Get your shakers ready! Rosa Mexicano is celebrating Valentine’s / Galentine’s at our winter cocktail class. Join us and test your bartending skills as you learn how to make some of Rosa’s new and signature cocktails, while enjoying our most popular snacks, including our world-famous guacamole. Perfect for couples looking for a unique activity or for groups of friends out for a Galentine’s celebration!
The Lil Chuck at the Charles Playhouse, Boston, February 13
Get ready for an unforgettable evening of laughs, tunes, and fierce friendship! This Galentine’s celebration blends comedy and music for a night that’s all about the power of sisterhood. Featuring hilarious stand-up from the sharpest comedians and unforgettable musical performances that’ll have you singing along (or laughing through tears), this show is a love letter to your besties. Whether you’re single, taken, or somewhere in between, this night is for YOU. Perfect for a night out with your squad—or anyone who makes your life sparkle—this event promises big laughs, catchy beats, and heartwarming vibes.
The Square Root, Roslindale, February 13
This event is brought to you free from the Roslindale Film Society and through generous financial contribution from The Boston Home Team and the Mass Cultural Council. In Casablanca, Morocco in December 1941, a cynical American expatriate meets a former lover, with unforeseen complications. A cinematic classic!
Valentine’s Beer Pairing Dinner
Castle Island Brewery and Bardo’s Bar Pizza, Boston, February 13
Celebrate Valentine’s Day with a special Beer Pairing Dinner! Indulge in a delightful evening filled with delicious food from Bardo’s Bar Pizza (and their sister company, Off the Vine Catering) expertly paired with a selection of craft beers from Castle Island Brewery. Whether you’re a beer connoisseur, food lover or just looking for a fun night out, this event is perfect for couples and friends alike. Join us for a memorable evening at Castle Island Brewery, 10 Old Colony Ave, South Boston. Check out the menu below.
Valentine’s Day Dining at Sogno
Sogno, Woburn, February 13
Treat your special someone to a cozy date night in our intimate, romantic space, and savor dishes crafted with the finest Italian ingredients. Whether it’s your first Valentine’s together or a cherished tradition, our warm ambiance and lovingly prepared cuisine create the perfect setting for an unforgettable evening. Reservations will fill fast, book your table today.
Valentine’s Day Dining at The Banks Seafood and Steak
The Banks Seafood and Steak, Boston, February 13 – 16
Celebrate love with your partner at The Banks Seafood and Steak restaurant. Indulge in a delicious Valentine’s Day dinner, available from February 13-16, 2025.
Valentine’s Day Dining at The Berkeley
The Berkeley, Boston, February 13 – 15
Celebrate love with a thoughtfully crafted three-course prix fixe dinner at The Berkeley. Indulge in dishes featuring fresh, seasonal ingredients, locally sourced to highlight the best of New England’s bounty. Enjoy chef-curated courses that pair perfectly with our bespoke cocktails and exceptional wine list.
Valentine’s Day Dining at The Bosworth
The Bosworth, Boston, February 13 – 15
Celebrate love with a dining experience featuring a menu crafted to set the tone for an unforgettable evening. Enjoy exclusively curated dishes by Chef Kinan Ibrahim, such as Beetroot Tartar and Filet Mignon with pan-seared foie gras, and Black Truffle Ravioli alongside specialty cocktail and champagne features.
Valentine’s Day Perfume Making Class
Boston Public Market, February 13
Join us at Bow Market for an intimate couples perfume workshop, a one-of-a-kind experience designed for you and your special someone. Guided by our skilled perfumer, you and your partner will embark on a sensory journey of rare essences and exclusive ingredients as you craft a bespoke fragrance that captures the essence of your unique love story and individual personalities. Enjoy a comprehensive class on how to create your own fragrance complete with wine and treats from local vendors. Each person leaves with a bespoke dry oil perfume, 4oz luxury lotion, or traditional perfume.
Time Out Market, Boston, February 14
Who says love is all you need? Join us for a night of anti-romance vibes with a live DJ spinning the best tracks to match your mood. Enjoy themed cocktails for purchase. Let’s celebrate singlehood, friendship, and living life on our own terms!
Paint & Sip: Paint Your Partner
Boston Public Market, February 14
Grab your partner and join us for a fun and creative evening of painting each other. Perfect for a Valentine’s Day date night! *1 drink (alcoholic or non-alcoholic) from the Pine Bar included with ticket purchase.
North of Boston
You don’t have to go all the way to Boston to experience good food and world-class museums. The Peabody Essex Museum in Salem is a great, underrated date spot. If your Valentine loves shopping, the antique stores along Main Street in Essex are a perfect stop. Or you can pretend you’re gilded-age magnates at Castle Hill on the Crane Estate.
North of Boston Events
Good Witch of Salem, February 14
Let’s have a Spa Day! Join us for a little pampering and relaxation with our Witch Apprentices. Children will create their own love potion and receive a sparkly nails, fancy hair accessories, a touch of glitter with pink lips and rosy cheeks.
Good Witch of Salem’s Love Potion
Good Witch of Salem, February 14
Fly into The Good Witch and Stay for a Spell! Step into the DIY Good Witch of Salem’s Potion Bar, where you can mix your very own magical potion creations! Choose your ingredients, sprinkle in magical moondust, add in your golden heart intentions, and seal with a special charm to take home the enchantment!
Salem Trolley, February 14
The most exciting way to spend the worst holiday is with the Salem Night Tour. With The Anti-Valentine’s Tour guests can bring a Valentine, friends, or go solo with us! This February 1st – 15th, we will focus on ghostly and darker stories of love gone wrong throughout Salem’s past. This year it will be on a trolley again!
The tour takes approximately 1 hour and 15 minutes and covers surprising, scandalous and often murderous stories of love gone wrong throughout Salem’s past. This annual event sells out quick, space is limited!
Valentine’s Day Dinner with Live Jazz Music at The Inn at Hastings Park
The Inn at Hastings Park, Lexington
Relax by a cozy fire, pop the champagne, and cue the jazz this Valentine’s Day at the Inn at Hastings Park, Boston area’s only Relais & Châteaux property located in historic Lexington, MA. Executive Chef Alissa Tsukakoshi creates a romantic four-course dinner pairing enchanting cuisine with delectable aromas with signature notes of favorite wines with live Jazz available all evening at Town Meeting Bistro, one of the few Boston-area restaurants with a fireplace!
South of Boston
Patriot Place in Foxboro is a great place to go shopping, grab a meal, and see a show. Or if you prefer something costal, Plymouth offers scenic views combined with history and great food.
South of Boston Events
Plimoth Cinema Valentine’s Day Dinner and a Movie
Plimoth Patuxet Museums, February 14
Join Plimoth Cinema for a delectable meal followed by a special showing of the classic romantic comedy P.S. I Love You. Dinner includes a glass of Prosecco, salad, and your choice of braised chicken with herb-crusted fingerling potatoes and thyme rosemary meyer lemon sauce, or a seared cauliflower steak with beluga lentils, harissa hummus, and lemon currant pistou. Dessert is a decadent flourless chocolate cake with raspberry coulis and vanilla bean whipped cream. Dinner begins at 5:30 p.m., followed by a 7 p.m. movie.
Valentine’s Tapas and Cocktails Lounge at The 1620 Winery at Cordage Park
1620 Winery at Crodage Park, Plymouth, February 14
Central Massachusetts
Wintertime is the perfect time to experience the beauty of Central Massachusetts. Get out and about Wachusett Mountain is hosting a number of specials and events for singles and couples throughout Valentines Day weekend. The architecture and public space of Worcester are must-see any time of year.
Central Massachusetts Events
Valentine’s Fireside Wine Dinner
Hardwick Winery, Hardwick, February 14
You are invited to join us at our Valentines/Galentines Fireside Feast at Hardwick Winery, a 5 course wine dinner in our 1795 Federal style mansion.
Learn the history of the mansion with Hardwick Winery owner John Samek, followed by a candlelit, fireside 5 course wine dinner prepared by Chef Peter Ryzewski, led by Sommelier and Wine Educator Missa Capozzo.
Teen Crafternoon – Valentines Day Scratch Art
Worcester Public Library, February 7
Whether you’re Team Valentine or Team Anti-Valentine, scratch art has something for everyone!
Teens can stop by the Frances Perkins branch on Friday, Feb 7th any time from 3:30 – 4:30 p.m. to get crafty with some scratch art hearts!
Dance Your Heart Out – Valentine’s Event
Barn at Blackston National, Sutton, February 7
The Barn at Blackstone National Family would like to invite you to our Annual Dance Your Heart Out event! On Friday, February 7th, 2025, at 5:30 pm – 10:30 p.m. Guests are encouraged to wear their Dance Party Best!
Cordella’s, Worcester, February 9
Join us at Cordella’s for a FREE family friendly crafter-noon! We will be making Valentine’s crafts hosted by our friend Emily Linhares! Sip on our new Valentine specialty drinks while creating crafts with your children or friends! There will be a variety of crafts for all skill sets.
Off the Rails, Worcester, February 14
Its A Date is New England’s hottest comedy dating show where four singles take the stage blindfolded and let their charms do the seducing, while the audience throws in deep and spicy questions. Get ready for a night where laughter, mystery, and unexpected sparks collide. Back to Worcester this Valentines day by popular demand!
Burncoat Center for the Arts and Wellness, February 13
Not finding the right glitter-caked Hallmark card for your person this year? Come make something more personal with your own two hands!
Join Amanda Santerre of The Golden Foxxe and create your own valentine.
Wittier Farms, Sutton, February 14
Since 2008, all the milk produced by Whittier Farms’ cows has been part of the Cabot Creamery Cooperative. Let’s show some Farm Love and have a Cheesy Date Night.
Enjoy an expansive selection of Cabot Creamery Cooperative cheeses, Boar’s Head meats, and homemade desserts with an interactive presentation from Whittier Farms’ staff. Hosted at The Milk Store.
After Hours: Valentine’s Date Night
Worcester Art Museum, February 14
Introducing your perfect date night. Make this Valentine’s Day memorable with a romantic evening out at the art museum. Explore the current exhibitions together and discover something new with that special someone. More information to come.
Be the first to see new exhibitions, explore themed events, and more, all After Hours. Spend your next night out at the Museum with music, drinks, and your fellow art lovers! View the full After Hours series.
Love Letters, presented by The Gilbert Players + The Center at Eagle Hill
The Center at Eagle Hill, Hardwick, February 14
Love Letters, a play by A. R. Gurney, follows Melissa Gardner and Andrew Makepeace Ladd III through their lives, by way of their letters exchanged. For more than 50 years, they correspond and grow together, confiding their hopes, dreams, triumphs, and disappointments in one another. They share a deep closeness that is at once charmingly funny and a poignant portrait of human connection. Starring Linda Tomasi (Co-Owner, The Gilbert Players) and Carl R. Mercier (Artistic Director, The Center at Eagle Hill).
Valentine’s Dinner at Polar Park
Polar Park, Worcester, February 14
Join us in Polar Park’s DCU Club on Friday, February 14, for a romantic Valentine’s Dinner where guests will enjoy a choice of filet, salmon, or Bolognese, with mashed potatoes, asparagus, and dinner roll, along with a strawberry field salad and choice of tiramisu or chocolate lava cake for dessert. Parties will have the option to add a bottle of wine or upgrade to a private suite to share with a significant other, friends, and family.
Black History Month: Recipe Swap
Worcester Public Library, February 21
In honor of Black History Month, come participate in a recipe swap at the Goddard Branch! Come with a family or cultural recipe in mind, make and decorate a recipe card, and swap it for someone else’s!
Cape Cod & the Islands
Don’t be fooled by winter weather – February is a perfect time to get out and about on Cape Cod and experience everything the area has to offer, away from the summer crowds. Many hotels, restaurants, and shops run off season specials.
Cape Cod & the Islands Events
Valentines Day in Paradise Comedy Show
Hyannis, February 14
Join us for our amazing Italian buffet starting at 7 p.m. and then laugh the night away with 3 of Boston’s top comedians.
Tables at 8 per table, unfortunately there are no other seating options.
Room packages are available by contacting the hotel.
Valentine’s at twenty-eight Atlantic
twenty-eight atlantic, East Harwich, February 14
Delight in an intimate candlelit five-course dinner at twenty-eight Atlantic featuring a specially crafted Valentine’s Day menu by Executive Chef James Hackney on the 14.
Chillmark, February 1
Stop by anytime between 2 to 4 p.m. to create a simple but festive Valentine’s garland. All ages welcome to this multigenerational workshop.
West Tisbury Library, February 14
Calling all kids! Join us on Feb. 14 for Pal-entine’s Day. What is Pal-entine’s day? It is a day for you! No partners necessary! We will have a nail salon, hair tinsel, decorate your own cupcake and more!
Come right off the bus from school, as the fun starts at 3 p.m. and continues until 4:40 p.m.
This event is free and open to ages 0 to 18. Children under 10 need to have an adult in the building. Under 8 needs adult at the program. Please email [email protected] with any questions.
Grange Hall, West Tisbury, February 14
In the spirit of love and community, Vineyard Preservation Trust invites you to a special Valentine’s Contra Dance at the historic Grange Hall! Celebrate the traditions of this cherished landmark while supporting its restoration. All are welcome—no experience or partner necessary! Festive colors like red and pink are encouraged!
Cape Cod Central Railroad, Hyannis, February 14
Romance on the Rails! Celebrate Valentine’s Day with your sweetheart and relax to the rhythms of the rails, while a fresh five-course gourmet meal is prepared and served on white table linens in traditional rail style.
Western Massachusetts
The art museums of Western Massachusetts – MASS MoCA, the Clark Art Institute, and the Williams College of Art are great places to spend an afternoon. Small but bustling downtowns like Shelburne Falls or Northampton offer perfect opportunities to take a walk or go shopping. Or you can get outside and go on a hike on Mount Greylock.
Western Massachusetts Events
Storrowton Tavern, Valentine’s Day
Storrowton Tavern, West Springfield
As Valentine’s Day approaches, we invite you to celebrate at our historic restaurant. Indulge in a delicious Sunday Brunch or make a traditional reservation for Friday, February 14. Our beautiful relaxed ambiance is the perfect setting for this occasion. Our awesome food and small town charm will make your experience unforgettable. Make your reservation by calling 413-732-4188 and let us be your destination for Valentine’s Day.
Delaney House, Valentine’s DayDelaney House, Holyoke
Make This Valentine’s Day Unforgettable at The Delaney House! Join us in the Delaney House ballroom on Friday, February 14 at 6:30 p.m. or Saturday, February 15 at 6:30 p.m.
Inn on Boltwood, Amherst
Celebrate love at 30Boltwood with a specially curated Valentine’s Day Prix Fixe menu, featuring delicious dishes designed to make your evening unforgettable. Our regular dining menu will also be available.
Champney’s Restaurant at the Deerfield Inn, Valentine’s Day
Deerfield Inn, Deerfield
Join us for a Valentine’s Day dinner! Reservations suggested.
TOPICS: Boston, Foxboro, Plymouth, Valentine's Day, Wachusett, West Springfield, Worcester
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