20 Romantic Things to Do in Massachusetts to Make Valentine’s Day Unforgettable

- Tuesday, February 10, 2026
Lallis & Higgins Insurance - Romantic Things in Valentine’s Day

Valentine’s Day is the perfect opportunity to surprise your loved one with something special. Whether you’re looking for classic romance, unique adventures, or cozy escapes, Massachusetts offers plenty of ways to celebrate. Here are ten great ideas for things to do around MA this Valentine’s Day!

  1. Enjoy a Candlelit Dinner in Boston’s North End
  2. Savor Italian cuisine and old-world charm in Boston’s famed “Little Italy.” Book ahead for a cozy table at one of the neighborhood’s beloved trattorias.
  3. Take a Romantic Stroll on Cape Cod Beaches
  4. Bundle up and walk hand-in-hand along the quiet winter shores of Cape Cod. Sunsets at Race Point Beach in Provincetown are especially breathtaking.
  5. Book a Spa Day in the Berkshires
  6. Relax together with a couples’ massage or spa package at one of the Berkshires’ luxurious resorts, such as Canyon Ranch or Cranwell Spa.
  7. Go Ice Skating on the Boston Common Frog Pond
  8. Glide across this iconic rink, then warm up with hot chocolate or a sweet treat from a nearby café.
  9. Take a Scenic Train Ride
  10. The Cape Cod Central Railroad or the Berkshire Scenic Railway offer picturesque winter excursions, some with special Valentine’s Day themes.
  11. Visit a Historic Inn for a Romantic Getaway
  12. Escape for a night or two to an inn like the Red Lion Inn in Stockbridge or the Captain’s House Inn in Chatham, both known for their New England charm.
  13. Sample Local Wines on a Vineyard Tour
  14. Massachusetts boasts several excellent wineries. Enjoy tastings and beautiful scenery at Nashoba Valley Winery, Mill River Winery, or Truro Vineyards.
  15. Catch a Show or Concert
  16. Treat your Valentine to live entertainment—whether it’s a Broadway show in Boston’s theater district or a concert at Symphony Hall.
  17. Take a Romantic Hike
  18. Explore scenic spots like Mount Greylock, the Blue Hills Reservation, or World’s End in Hingham for crisp air and stunning views.
  19. Indulge in Sweet Treats from a Local Chocolatier
  20. Visit a specialty chocolate shop such as LA Burdick in Cambridge or Taza Chocolate in Somerville for locally made confections to share with your sweetheart.

Whether you’re seeking relaxation, adventure, or classic romance, there’s something for every couple in Massachusetts this Valentine’s Day. Happy celebrating!

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