Happy Thanksgiving Weekend from Robert Paul Properties

8 Things To Do Thanksgiving Weekend from Boston to Cape Cod

Thanksgiving brings the warmth of family, delicious feasts, and cherished traditions. But for those who prefer to avoid the chaotic crowds of Black Friday shopping, we’ve got you covered. Whether you’re in the mood for a history-rich outing, a touch of holiday sparkle, or some lighthearted fun, here are eight great ways to spend Thanksgiving weekend from Boston to Cape Cod. From retracing the Pilgrims’ steps to watching sugarplum fairies twirl in The Nutcracker, there’s something for everyone.

Eight Fun Thanksgiving Weekend Activities

1. Annual Lighting of the Pilgrim Monument

Annual Lighting of the Pilgrim Monument

Retrace the Pilgrims’ footsteps in Provincetown, where they first landed on November 21, 1620. The Pilgrim Monument, built in 1910, stands as a tribute to this significant moment. Join the community as the monument lights up with over 3,000 lights in a dazzling ceremony.

  • When: Wednesday, November 27, 5–7 PM
  • Where: Pilgrim Monument & Provincetown Museum, 1 High Pole Hill Rd, Provincetown, MA
  • Tickets: Free admission

2. Holidays at Highfield Hall

Experience the holiday season with elegance at Highfield Hall in Falmouth. The historic venue transforms into a sensory delight with festive music, art displays, seasonal treats, and beautifully arranged greenery. Don’t miss the handcrafted art for sale at the Gift Gallery or the model train and crèche exhibits.

  • When: November 22–December 15, 10 AM–4 PM (Friday–Sunday), 12 PM–4 PM (Monday–Thursday)
  • Where: Highfield Hall & Gardens, 56 Highfield Dr, Falmouth, MA
  • Tickets: $20 for adults, $15 for members; free for children and military

3. The Train to Christmas Town

Get into the holiday spirit aboard the Train to Christmas Town. This magical journey, based on the beloved children’s book, brings the story to life with interactive games, character visits, and sing-alongs. Keep an eye out for friendly animal characters hidden throughout the train!

  • When: November 22–December 23
  • Where: Departs from Buzzards Bay Depot, 70 Main St, Buzzards Bay, MA
  • Tickets: $64–$114 for adults, $54–$104 for children

4. Gardens Aglow at Heritage Museum and Gardens

Gardens Aglow at Heritage Museum & Gardens, Sandwich, MA

Michelle K Callahan, CC BY 2.0, via Wikimedia Commons

Step into a winter wonderland at Heritage Museum and Gardens in Sandwich, where over 10 miles of lights illuminate the grounds. The event also features holiday-themed indoor décor, activities, and beautiful garden displays.

  • When: Select Nights, November 29–December 23, 4:30 PM–8 PM
  • Where: 67 Grove St, Sandwich, MA
  • Tickets: $25 for adults, $13 for children, members receive discounts

5. Thanksgiving Day Hunt with Norfolk Hunt Club

Start your Thanksgiving morning with an exciting community tradition. The Norfolk Hunt Club’s Thanksgiving Day Hunt brings together spectators to see hounds, riders, and horses as they set off from the Steeplechase Course in Medfield.

  • When: November 28, 9–10 AM
  • Where: 240 North Street, Medfield, MA

6. Gobble Gobble Gobble Thanksgiving Weekend Race

Run off those holiday indulgences at the annual four-mile Thanksgiving Day race in Somerville. Open to runners of all ages, the race supports local charities and encourages a fun, active start to the holiday.

  • When:  November 28, 9 AM
  • Where: Davis Square, Somerville, MA
  • Tickets: $45–$49 registration fee

7. Boston Ballet’s The Nutcracker

Boston Ballet's The Nutcracker

Immerse yourself in the timeless magic of The Nutcracker performed by the Boston Ballet. This iconic show, with Tchaikovsky’s enchanting score and stunning choreography, is a perfect holiday tradition.

  • When: November 29–December 29
  • Where: Citizens Bank Opera House, 539 Washington St, Boston, MA
  • Tickets: Please visit the website for pricing information

8. Thanksgiving Dining at Plimoth Patuxet

Experience a historically inspired Thanksgiving meal at Plimoth Patuxet (formerly Plimoth Plantation). Enjoy a buffet filled with seasonal dishes and engage in the history of the first Thanksgiving.

  • When: November 29, 12 PM–6 PM
  • Where: 137 Warren Ave, Plymouth, MA
  • Tickets: $85 for adults, $43 for children under 12 (member discounts available)

Thanksgiving Weekend Fun for All!

Thanksgiving weekend is the perfect time to embrace the festive spirit with a variety of exciting events from Boston to Cape Cod. Whether you’re immersing yourself in history, enjoying holiday lights, or getting active with a Turkey Trot or 5K, there’s no shortage of fun ways to celebrate. From shopping local at holiday markets to experiencing the magic of The Nutcracker or a train ride to Christmas Town, there’s something for everyone to enjoy and make lasting memories. Start planning your Thanksgiving weekend today!

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