Best Christmas Attractions and Experiences in Boston 2026

Boston offers a full lineup of Christmas attractions and experiences for all ages, from Santa visits and festive marathons to carriage rides, wine tastings, and holiday cruises. Take a look at the events that make Boston a standout destination for celebrating the season in 2026!

The Best Christmas Attractions and Experiences in Boston This Season

Beyond the traditional events, Boston offers a handful of standout experiences worth building your season around. Here are the top Christmas attractions in Boston to add to your must-visit list this season!

1. Holiday Wine Festival at Vaillancourt Folk Art — Sutton

Tailored specifically for those hosting holiday dinners or hunting for distinct host gifts, this inaugural tasting event at Vaillancourt Folk Art focuses on the logistics of winter entertaining. Conducted in partnership with Ruby Wines, this adults-only gathering features an educated pour of premium labels curated to complement traditional autumn and winter menus. Sommeliers and distributors remain on hand to talk through flavor profiles, helping you plan exactly what to serve alongside everything from Thanksgiving turkey to Christmas roasts.

• Dates: Saturday, November 7th, 2026 
• Admission: Ticketed (Strictly 21+; identification required at the door)
• Street Address: Vaillancourt Folk Art, 9 Main Street, Suite 1-H, Sutton, MA 01590
• Kid Friendly: No
• Pet Friendly: No
• Parking: Free parking available in the main facility lot
• Website: https://valfa.com/event/holiday-wine-festival/

Insider Tip: This event is a buying opportunity as much as a tasting. Come prepared with a digital list of your holiday menus so you can consult directly with the Ruby Wines representatives to build a custom beverage blueprint for your gatherings.

2. Yuletide Wine Garden at Vaillancourt Folk Art — Sutton

This recurring open-air lounge at Vaillancourt Folk Art provides a relaxed, self-paced escape from the rush of holiday shopping. Popping up every weekend from Black Friday through the final days before Christmas, the courtyard serves authentic Nuremberg Glühwein, a spiced, hot mulled wine kept at a perfect simmer, alongside crisp seasonal beers and mimosas. The culinary pairing leans heavily into Old World street food, highlighting traditional German sausages and warm, rolled chimney cakes from Frauleins Bakery.

• Dates: Friday, November 27th & Saturdays and Sundays from November 28th through December 20th, 2026
• Admission: Free entry (Food and beverages purchased individually)
• Street Address: Outdoor Pavilion at Vaillancourt Folk Art, 9 Main Street, Suite 1-H, Sutton, MA 01590
• Kid Friendly: Yes
• Pet Friendly: Yes (welcoming for leashed dogs in the open-air pavilion)
• Parking: Ample free parking within the main gallery grounds
• Website: https://valfa.com/event/yuletide-wine-garden/

Insider Tip: If you want to beat the cold, the heat lamps in the pavilion are most effective along the eastern wall. Snag a seat there early, order a mug of Glühwein, and pair it with a cinnamon dusted chimney cake before the bakery line builds after lunchtime.

3. A Vaillancourt Viking Christmas Cruise On The Rhine — International

An exceptional long-form travel opportunity designed for heritage art collectors who want to trace the geographic roots of modern holiday traditions, this Vaillancourt Folk Art exclusive eight-day river voyage charts a course through four European countries along the Rhine Valley. The journey focuses heavily on cultural immersion, taking travelers past the intricate storefront architectures of Cologne, into centuries-old wine cellars, and directly through traditional town-square markets packed with handcrafted woodwork and regional glass ornaments.

• Dates: Departing Wednesday, December 2nd, 2026 (8-day international voyage)
• Admission: Ticketed (Requires advanced registration, deposits, and valid passports)
• Street Address: Departs from European port (Group travel coordination available from Boston)
• Kid Friendly: Best suited for adults and older teens with an interest in history
• Pet Friendly: No
• Parking: Long-term airport parking rates apply based on your departure flight
• Website: https://valfa.com/event/a-vaillancourt-viking-christmas-cruise-on-the-rhine/

Insider Tip: European winter river currents can occasionally alter docking times slightly. Keep your daily schedule flexible and prioritize packing layers that protect against damp, moving river winds rather than just heavy dry snow.

4. Nantucket Festival of Trees — Nantucket

Step off the ferry and straight into a glowing winter sanctuary that transforms the heart of downtown Nantucket into an immersive gallery of seasonal artistry. Each December, the Whaling Museum is filled with a dense forest of uniquely designed holiday trees, each hand decorated by local merchants, resident artists, community groups, and island school children. The historical exhibits serve as a dramatic backdrop for the displays, creating a striking visual dialogue between Nantucket’s maritime heritage and modern holiday creativity. It stands as a foundational community benefit event that captures the close knit charm of island life at its absolute finest.

• Dates: December 5th, 2026 through December, 31st, 2026
• Admission: Ticketed
• Street Address: Whaling Museum, 13 Broad Street, Nantucket, MA 02554
• Kid Friendly: Yes
• Pet Friendly: No
• Parking: Limited street parking available downtown; walking or using public island transport is highly encouraged
• Website: https://nha.org/join-give/benefit-events/festival-of-trees/

Insider Tip: The natural light streaming through the museum's large windows creates a stunning backdrop for the trees at midday. Visit during the early afternoon to capture the most vibrant photos of the custom ornaments before the indoor lighting takes over.

5. Christmas in Salem Weekend — Salem

Peel back the layers of history and step inside the beautifully preserved architectural gems of one of America's oldest coastal communities. This exclusive holiday house tour grants visitors rare, behind the scenes access to a curated selection of Salem's private historic homes, each meticulously dressed in elegant, creative seasonal decor by local designers and homeowners. Beyond the rare glimpse into classic Federal, Colonial, and Victorian interiors, the weekend features festive community pop-ups, historic storytelling, and local holiday cheer. It stands as an absolute must visit destination for design lovers, history buffs, and anyone seeking a deeply authentic New England holiday experience.

• Dates: Saturday, December 5th, 2026 & Sunday, December 6th, 2026
• Admission: Ticketed (Advanced online ticket purchase required)
• Street Address: Various Historic Neighborhoods, Salem, MA 01970
• Kid Friendly: Yes
• Pet Friendly: No (Private historic residences are strictly restricted to service dogs)
• Parking: Public parking garages available downtown at Church Street and South Harbor
• Website: https://historicsalem.org/events/christmas-in-salem-weekend/

Insider Tip: These are real, historic private residences with narrow entryways and delicate flooring. Wear comfortable slip-on walking shoes to make house transitions effortless, and leave bulky backpacks or large bags in your car to avoid navigating tight spaces.

6. Jingle Bell Half Marathon & 5K — Haverhill

Embrace the title of the "Merriest Run in New England" and inject some high-energy holiday cheer directly into your winter training schedule. This long running regional favorite guides runners and walkers through gorgeous, crisp New England landscapes as a chorus of jingling bells sounds out along the course. The festive atmosphere is amplified by participants sporting full holiday gear, spreading seasonal joy with every mile logged. The real reward waits at the finish line, where a massive, ho-ho-holiday themed post race party serves up hot beverages and an array of festive snacks that would make Santa proud.

• Dates: Sunday, December 6th, 2026
• Admission: Paid (Advanced online registration required)
• Street Address: Sports and Fitness Center at Northern Essex Community College, 100 Elliott Street, Haverhill, MA 01830
• Kid Friendly: Yes
• Pet Friendly: No
• Parking: On-site event parking available at designated race staging lots
• Website: https://jinglebellhalf.com/

Insider Tip: Holiday costumes are a huge part of the fun here, but New England December mornings can be unpredictable. Wear technical sweat wicking layers underneath your festive gear to stay dry and warm as you tackle the open course miles.

7. Frosty Half-Marathon — Raynham

Conquer the winter elements and join a dedicated community of runners for a beautifully organized, classic road race through the quiet residential lanes of Raynham. Back for its 14th year, this scenic half-marathon course offers an excellent mix of minimal to moderate elevation changes on country roads, featuring a rewarding, challenging hill at mile 10 to perfectly prime your legs for a fast finish. The event prioritizes runner safety and comfort from start to finish, boasting an indoor pre and post-race headquarters. The true highlight of the morning is the celebratory finish, where every runner is treated to a full, hot cooked breakfast and access to warm showers.

• Dates: Sunday, December 6th, 2026 
• Admission: Paid 
• Street Address: Raynham Middle School, 420 Titicut Road, Raynham, MA 02767
• Kid Friendly: Yes (excellent for families to spectate and enjoy the indoor facility)
• Pet Friendly: No
• Parking: Plenty of free parking located directly adjacent to the start/finish line at the middle school fields
• Website: https://runsignup.com/Race/MA/Raynham/FrostyHalfMarathon

Insider Tip: There is a strict 3 hours course limit enforced by town public safety (a 14 minutes mile pace). If you need extra time to complete the 13.1 miles, make sure to coordinate with race officials ahead of time to utilize the official early start option.

8. Jingle Bell Run Central MA — Worcester

Turn your holiday energy into powerful action at the most spirited 5K of the holiday season. The Jingle Bell Run Central MA invites runners, walkers, and pacing crews of all skill levels to tie bells to their shoelaces and don their favorite holiday costumes. Far more than just a celebratory winter jog, this long standing holiday tradition creates momentum and real world solutions for the millions of adults and children living with arthritis. Every dollar raised through individual registration, team rallies, and community donations goes directly to support the vital research, patient advocacy, and community programs led by the Arthritis Foundation.

• Dates: Saturday, December 5th, 2026 
• Admission: Paid 
• Street Address: Bay State Brewing / Worcester Common area, 112 Harding St, Worcester, MA 01604
• Kid Friendly: Yes (Perfect for a family stroll or run)
• Pet Friendly: Yes (leashed dogs are welcome)
• Parking: Ample public parking lots and municipal garages available throughout the Worcester Common and Canal District areas
• Website: https://events.arthritis.org/jbrcentralma

Insider Tip: Electronic chip timing is included in the timed tier for competitive runners. Grab your packet early to secure your bells and tie them tight so you can join the cheerful chorus of thousands of jingling sneakers hitting the road.

9. Beverly Reindeer Run 5K — Beverly

Kick off the holiday season by running, walking, or prancing through Beverly’s scenic coastal roads and historic downtown. This spirited 5K road race focuses heavily on grassroots community impact, reinvesting 100% of registration fees, fundraising tiers, and donations into essential financial assistance and programming scholarships. The course comes alive with Santas, elves, and reindeer costume wearers, making it a highly visual and festive event. Every registration helps provide immediate resources to the families and individuals who need the community most, fully organized and backed by the YMCA of the North Shore.

• Dates: Saturday, December 5th, 2026 
• Admission: Paid 
• Street Address: First Baptist Church (Back parking lot on Hale St), Cabot Street, Beverly, MA 01915
• Kid Friendly: Yes
• Pet Friendly: Yes (Leashed dogs are fully welcome)
• Parking: Street parking is available along Cabot Street and neighboring side streets
• Website: https://raceroster.com/events/2026/112621/greater-beverly-ymca-reindeer-run-5k-road-race

Insider Tip: Special medals are awarded to the top three in standard age groups, plus local honors for the fastest Beverly residents.

10. Happy Holidays Half MerryThon & 5K — Gloucester

Celebrate the holidays in sneakers while soaking in spectacular ocean views along the Cape Ann coastline. Commemorating YuKan Sports' 15th anniversary, this beautifully scenic, USATF-sanctioned winter race offers both a 5K and a certified Half Marathon. Runners share the road with seasonal characters like reindeer and elves, culminating in an energetic finish line celebration at Good Harbor Beach featuring delicious pizza and baked holiday treats.

• Dates: Sunday, December 6th, 2026 
• Admission: Paid 
• Street Address: Good Harbor Beach, 99 Thatcher Rd, Gloucester, MA 01930
• Kid Friendly: Yes 
• Pet Friendly: No (Per USATF rules, dogs, strollers, and wheels are strictly prohibited on this open road course)
• Parking: Free parking on-site at the main beach parking lot; an overflow lot is available 3/4 mile away on Nautilus Road
• Website: https://www.yukanrun.com/happy-holidays-half-merrython-5k

Insider Tip: When parking at the beach lot, park on the far front or back rows. High tide frequently forms a massive puddle right in the center of the lot, which volunteers will block off with traffic cones. Register by November 9th to get your name custom printed on your race bib.

11. Medfield Foundation Angel Run — Medfield

Entering its 21st annual edition, the Angel Run is a heartwarming suburban holiday tradition that gathers over 1,400 runners, walkers, and volunteers. This USATF certified 5K route is packed with holiday themes, winter decorations, live musicians, and enthusiastic neighborhood crowds. Founded originally to honor the memory of local resident Natasha Domeshek, the race has raised nearly $300,000 for the Community Assistance Fund. These critical winter crisis funds are distributed directly to local residents facing sudden hardships through an application process administered by The Medfield Foundation.

• Dates: Sunday, December 6th, 2026 
• Admission: Paid 
• Street Address: Medfield High School, 88R South St, Medfield, MA 02052
• Kid Friendly: Yes 
• Pet Friendly: Yes (Leashed dogs are highly encouraged to join the costume fun)
• Parking: Free on-site parking is available at both Medfield High School and the adjacent Blake Middle School
• Website: https://www.medfieldfoundation.org/angelrun

Insider Tip: There is no separate corral for competitive athletes, so if you are running for a specific PR, make sure to position yourself right at the front of the starting line before the 11:30 AM gun.

12. Winter Classic 5K — Cambridge

Brace the chilly December air for one of the most popular and energetic holiday road races in the Boston metro area. The Winter Classic 5K starts and finishes in beautiful downtown Cambridge, sending thousands of runners in festive attire sprinting or strolling down Massachusetts Avenue. Because the urban course is incredibly flat, participants can crush their personal records and head straight to the legendary post race party to toast the winter season.

• Dates: Sunday, December 6th, 2026 
• Admission: Paid 
• Street Address: 64 Sidney St, Cambridge, MA 02139
• Kid Friendly: Yes (Strollers are permitted but should line up toward the back for safety)
• Pet Friendly: No
• Parking: Very limited street parking in downtown Cambridge; taking the MBTA Red Line directly to Central Square Station is highly recommended
• Website: https://runsignup.com/Race/MA/Cambridge/WinterClassic5K?aflt_token=vkmwDmweQ4iCYn8otSOOnKQ3vCO8buOw

Insider Tip: This event is notorious for selling out weeks in advance due to the popularity of its post race party. Prices increase sharply after October 12th, so secure your group's registration early in the autumn to lock in the best rate.

13. Chocolate Marshmallow 5K/10K — Seekonk

Enjoy a brisk winter run through the peaceful, scenic countryside of Seekonk right on the Rhode Island border. Celebrating its 4th annual event, this race offers a chip-timed 5K and 10K courses. The ultimate highlight of the morning is the cozy finish line reward: a gourmet spread of steaming hot chocolate, plush marshmallows, and holiday goodies waiting to warm everyone up.

• Dates: Sunday, December 6th, 2026
• Admission: Paid
• Street Address: Seekonk YMCA, 473 Taunton Ave, Seekonk, MA 02771
• Kid Friendly: Yes
• Pet Friendly: No
• Parking: Ample free parking available right on-site within the main Seekonk YMCA parking lots
• Website: https://www.active.com/seekonk-ma/running/distance-running-races/chocolate-marshmallow-5k-10k-2026?afid=156210&ltcmp=254301&ltclickid=07_229724605_6c293743-447f-4ab7-9486-4b6687ec30e9&cmp=39N-DP260-BND10-SD230-DM20&cdg=affiliate-254301

Insider Tip: Packet pickup is strictly available on race day morning inside the YMCA starting at 6:30 AM. Arrive by 7:15 AM at the latest to grab your bib, attach your timing chip, and avoid the pre-race registration lines.

14. TARC Winter Classic — Stoneham

Embrace the rugged beauty of a classic New England winter trail run at the TARC Winter Classic. Hosted by the largest ultra-running community in the Northeast, this premier event sends runners deep into the scenic woods of the Middlesex Fells Reservation along the historic Skyline Trail. Participants can choose between an 8 miles single loop, a grueling 32 miles ultra, or the ultimate 40 miles challenge, all featuring rolling elevation changes, dense roots, and rocky single track. True to tradition, the race kicks off with a massive, collective "Yeti Howl" at the starting line. Every registration directly helps fund public trail preservation and open-space conservation through a direct partnership with the Friends of the Fells.

• Dates: Saturday, December 5th, 2026
• Admission: Paid
• Street Address: Fallon Road (Start/Finish area), Stoneham, MA 02180
• Kid Friendly: Yes (Highly supportive of young trail runners)
• Pet Friendly: No (Pets are not permitted on the course)
• Parking: Free parking is located at 4 N Border Road, Stoneham, MA 02180.
• Website: https://www.findtherun.com/race/126086/tarc-winter-classic

Insider Tip: This is a strictly cup-less race. Bring your own hydration pack or reusable flask. If you are tackling the 32-mile or 40-mile ultras, pack a high-powered headlamp, as a working light is required if your final loop stretches into sunset.

15. Santa Claus Shuffle — Manchester, NH

Paint the town red at the Santa Claus Shuffle, a vibrant holiday tradition that transforms the streets of Manchester into a sea of running Santas. Presented by Millennium Running, this high energy 3 miler/5K road race includes a full Santa suit (hat, beard, jacket, pants, and belt) with every adult registration, making for an incredible festive environment. Perfect for the whole family, the event also features a dedicated "Lil' Elf" youth dash for the little ones, keeping the holiday spirit moving for runners of all ages.

• Dates: Saturday, December 5th, 2026 
• Admission: Paid
• Street Address: 700 Elm St., Manchester, NH  03101
• Kid Friendly: Yes
• Pet Friendly: No (Pets are not allowed on the race course)
• Parking: Ample downtown street and garage parking available near the start/finish line
• Website: https://www.runreg.com/13310

Insider Tip: This isn't your standard morning jog, you are running alongside a literal tidal wave of thousands of identical Santas. To keep track of your family or friends in the crimson sea, have everyone wear bright, matching neon socks or unique holiday glasses so you can actually spot each other at the starting line.

16. Woo Jingle 5K & Kids Run — Worcester

Kick off the holiday season in the heart of Central Massachusetts at the Woo Jingle 5K. Starting and finishing right next to Worcester City Hall on Front Street, this energetic event features a fast 5K run/walk and a dedicated Kids Run. Festive costumes are highly encouraged, and the holiday cheer continues long after the finish line with a lively post race party. The race also serves as the proud first leg of the Greendale Physical Therapy Worcester Triple Crown 5K series. Every registration helps collect toy donations and funding for families in need through a close partnership with the Plant a Seed Foundation.

• Dates: Sunday, December 6th, 2026 
• Admission: Paid
• Street Address: Front Street (Next to Worcester City Hall), Worcester, MA 01608
• Kid Friendly: Yes
• Pet Friendly: No (Pets are strictly prohibited on the course)
• Parking: Convenient parking is available at the Worcester Common Garage and surrounding downtown surface lots
• Website: https://runsignup.com/Race/MA/Worcester/WooJingle5K 

Insider Tip: Spread some holiday kindness by bringing a new, unwrapped toy to packet pickup (Saturday at Sneakerama from 11 AM to 5 PM) or directly to the starting line on morning race. All collections go directly to the Plant a Seed Foundation to support local families in need.

17. 9th Annual Winter SOLEstice 5K Run/Walk — Wilmington

Embrace the crisp December air at the Winter SOLEstice 5K, a wonderfully inclusive community race hosted by the Sole Sisters Running Club. This USATF-certified 5K course is explicitly designed to welcome every pace, providing a highly supportive environment for both competitive athletes aiming for a personal best and families enjoying a seasonal stroll. Cash prizes and distinct awards are handed out to the top three overall male, female, and non-binary finishers, alongside traditional age group crowns.

• Dates: Saturday, December 12th, 2026 
• Admission: Paid
• Street Address: 159 Church Street, Wilmington MA
• Kid Friendly: Yes (Strollers are welcome)
• Pet Friendly: No (Due to safety regulations on the course, pets are not allowed)
• Parking: Free on-site parking available at the race staging area
• Website: https://runsignup.com/Race/MA/Wilmington/SOLEstice5K 

Insider Tip: Skip the $45 race-day price premium by locking in your spot online before registration closes on Wednesday, December 9th. If you're walking with a stroller or little ones, hang out near the back of the starting corral. The Sole Sisters keep the vibe incredibly supportive, so you'll have plenty of room to cruise once the pack thins out.

18. The Mount Hood Nutcracker Challenge — Melrose

Celebrating its 20th edition, this beloved December tradition turns cross country running into a holiday celebration at the scenic Mount Hood Golf Club. Organized by the Melrose Running Club, this event features a unique 3.5 mile cross country race along rolling fairways and pathways, alongside a non-competitive 2 mile walking route. Known for its dynamic element where the course layout changes every single year, the event draws competitive runners vying for coveted nutcracker trophies as well as participants festively dressed in holiday attire. The race caps at 250 participants and hosts a post race gathering at the Melrose Fish & Game Club, with proceeds directly benefiting local cross country youth programs and Housing Families, Inc., which fights to prevent eviction and provide emergency shelter.

• Dates: Saturday, December 12th, 2026 
• Admission: Paid (Registration details available on the main portal)
• Street Address: Melrose Fish & Game Club, 100 Slayton Road, Melrose, MA 02176
• Kid Friendly: Yes 
• Pet Friendly: No (Pets are not permitted on the cross country course)
• Parking: Primary event parking is located closer to the main Mount Hood Golf Clubhouse. Plan for a short, brisk ⅓ mile warm-up jog up Stillman Road to reach the Fish & Game Club venue
• Website: https://runsignup.com/Race/MA/Melrose/TheMountHoodNutcrackerChallenge 

Insider Tip: Strollers are strictly banned due to the rugged, unpredictable cross-country terrain. Since the primary parking lot is closer to the golf clubhouse, treat the 1/3-mile uphill trek to the Melrose Fish & Game Club as your official race warm-up.

19. Bill Rodgers Somerville Jingle Bell Run & Walk — Somerville

Step up to the starting line of one of Greater Boston’s most wildly popular holiday events at the Bill Rodgers Somerville Jingle Bell Run. This 5K winds through the historic streets and squares of Somerville before circling back to finish right in the heart of Davis Square. It’s legendary for its unmatched post race atmosphere, partnering with an incredible lineup of local pubs, bars, and saloons, including The Burren, Olde Magoun Saloon, and The Foundry on Elm, for a city wide celebration.

• Dates: Sunday, December 13th, 2026 
• Admission: Paid (Advance online registration required)
• Street Address: Davis Square, Elm Street, Somerville, MA 02144
• Kid Friendly: Yes 
• Pet Friendly: No (Heavy crowds and tight city streets make this course unsuitable for pets)
• Parking: Extremely limited street parking around Davis Square; taking the MBTA Red Line directly to the Davis Station stop is highly recommended
• Website: https://runsignup.com/Race/MA/Somerville/BillRodgersSommervilleJingleJog 

Insider Tip: This event has a strict registration cap and absolutely zero race day registration once it fills up. Set a calendar reminder to sign up early so you don't miss out on the legendary post race pub tour.

20. Downtown Jingle 5K — Providence, Rhode Island

Ring in the holidays with a Christmas road race at the annual Downtown Jingle 5K. Held along the scenic riverfront on Memorial Boulevard, this race brings together serious runners, casual walkers, and kids for a morning of absolute holiday cheer. All participants are fully chip-timed, and online registrants are guaranteed a custom event t-shirt. The morning kicks off with a spirited Kids Elves Run, followed by the main 5K, with local sponsors like Marathon Sports keeping the energy high. Every year, the event collects holiday toy donations directly at packet pickup to support the regional Toys for Tots program.

• Dates: Sunday, December 13th, 2026
• Admission: Paid 
• Street Address: 10 Memorial Boulevard, Providence, RI 02903
• Kid Friendly: Yes (Features a dedicated Kids Elves Run for boys and girls with special top three trophies)
• Pet Friendly: No (Pets must stay home)
• Parking: Convenient parking is available right at the Providence Place Mall garage, located immediately adjacent to the packet pickup zone
• Website: https://runsignup.com/Race/RI/Providence/DowntownJingle5K

Insider Tip: Go to the pre-race pickup at Marathon Sports (Providence Place Mall, Level 1) on Friday or Saturday from 12 to 6 PM. You can drop off your Toys for Tots donation early and score easy mall parking before Sunday's crowds arrive.

21. Santa's Toy Trot — Merrimac

Hosted by the Winner's Circle Running Club, Santa's Toy Trot brings a vibrant blast of holiday cheer to the charming streets of Merrimac with an innovative, loop based course. Starting and finishing at the Sweetsir School, participants tackle a flat, paved, and completely stroller friendly 2 mile loop, giving runners the strategic freedom to finish after one, two, or three laps to complete a 2, 4, or 6 miles distance. The community centric event also features a free "Elves Fun Run" around the school grounds for children under 10, complete with holiday characters and finish-line gifts. Embracing a lively "Ugly Christmas Sweater" theme with prizes for the most outrageous outfits, the chip-timed event raises essential funds and collects toy donations to support the Merrimac Holiday Helper Program for local families.

• Dates: Sunday, December 13th, 2026 
• Admission: Paid 
• Street Address: 104 Church Street (Sweetsir School), Merrimac, MA 01860
• Kid Friendly: Yes (Includes a completely free Elves Fun Run for children aged 10 and under, safely guided by a club member)
• Pet Friendly: No (Pets are not permitted on the running loops)
• Parking: Free parking is available directly in the Sweetsir School main lot and designated adjacent school zones
• Website: https://runsignup.com/Race/MA/Merrimac/WCRCSantaToyTrot246

Insider Tip: Dig into the back of your closet for something fun to wear! The event actively encourages participants to sport their most outrageous, over the top Ugly Christmas Sweaters on the course. Make sure to register early, as only the first 200 entrants are guaranteed to receive the exclusive race day giveaway.

22. 3rd Annual Cousin Eddie's Christmas Run 5K — Plymouth

Channel your inner holiday comedy legend at the "hap-hap-happiest" Christmas run of the season. Hosted at the Mayflower Brewing Company, this wildly fun 5K is entirely dedicated to celebrating a classic holiday comedy. Runners can choose to dress up in their own festive gear or select the ultimate registration tier to receive a full Cousin Eddie costume to wear along the course. It’s a morning packed with laughs, community camaraderie, and great local craft beer.

• Dates: Sunday, December 20th, 2026 
• Admission: Paid 
• Street Address: Mayflower Brewing Company, 12 Resnik Road, Plymouth, MA 02360
• Kid Friendly: Yes (A highly lighthearted jog/walk experience perfect for families)
• Pet Friendly: No (The crowded brewery grounds and race course are restricted for pets)
• Parking: Free parking is available in the main Mayflower Brewing lot and along designated industrial park complex roads
• Website: https://www.wickedfastraces.com/cousin-eddies-christmas-run-5k

Insider Tip: If you want to fully look the part without building your own costume, select the 'Jelly of the Month Club' registration tier. It comes fully loaded with a green bomber-style winter hat and a white bathrobe so you can run alongside hundreds of other Eddies.

23. 2026 Unified 5K Remote & AdaptXpo — Lancaster (Virtual)

The Annual Unified 5K and AdaptXpo stands as a hallmark of inclusivity, community strength, and adaptive sports education. Staged remotely out of Lancaster, this highly accessible virtual road race is uniquely designed so that individuals of all abilities can participate together from anywhere, whether they choose to run, walk, roll, or row. Offering a standard 5K or a Mile route, the event proactively accommodates different paces and comfort levels. The event raises critical funds for AdaptX research, education, community programming, and grant initiatives, ensuring that fitness and sport are accessible to everybody. 

• Dates: Thursday, December 31st, 2026 (Run, walk, or roll your distance anytime on New Year's Eve)
• Admission: Paid (All registration tiers directly support adaptive sports education and community programming grants)
• Street Address: Remote / Virtual Event (Staged out of Lancaster, MA 01523)
• Kid Friendly: Yes (An incredible opportunity for kids to learn about adaptive sports and participate at their own comfortable distance)
• Pet Friendly: Yes (Since this is a fully virtual event, your favorite four-legged training partners are welcome to join your route!)
• Parking: N/A (Participate from your own neighborhood trail, local track, or favorite park path)
• Website: https://runsignup.com/Race/MA/Lancaster/Unified5KRemote

Insider Tip: This virtual race is fully verified and counts towards major regional running accomplishments, including the Run Rhody Grand Slam, the Greendale Physical Therapy Worcester Triple Crown, and the Tour de Patrick series.

Tips for Christmas Attractions and Experiences in Boston

• Book Santa photos early: Popular Santa visits at malls, train rides, and holiday villages sell out weeks in advance. Book as soon as dates are announced.
• Plan around nap and meal times: Holiday events draw crowds at peak times. Going right at opening or in the late afternoon often works better for younger kids.
• Layer up for outdoor events: Many Christmas attractions are partially or fully outdoors. Bring extra layers, hats, and gloves for unpredictable weather.
• Bring snacks: Food at holiday events often has long lines and inflated prices. Packing your own snacks saves money and meltdowns.

Frequently Asked Questions

Here's what to know before you go to any of the listed Boston experiences and attractions this season.

What are the best Christmas activities for kids in Boston?

Boston offers everything from Santa visits and ice skating to holiday train rides, holiday 5ks, and interactive Christmas villages. The right pick depends on your kids' ages and interests. Check individual listings for age recommendations.

Where can I take a photo with Santa in Boston?

Major shopping centers, holiday villages, train experiences, and select neighborhood events offer photos with Santa. Reservations are strongly recommended for the most popular Santa visits, which book up weeks in advance.

Are Boston Christmas activities free for kids?

Most Christmas experiences in Boston are ticketed events, but many offer reduced prices for children. Check individual listings for details.

When should I book Christmas attractions and experiences in Boston?

Book ticketed activities as soon as dates are announced, typically in October. The closer to Christmas, the harder tickets are to get.

Can I add my event to this guide?

We'd love to feature your Christmas event! Simply share your event through our quick submission form and we will get it added to the list!

Christmas Attractions and Experiences Worth the Drive from Boston

Boston isn't the only place worth visiting for Christmas attractions and experiences this season. Within a couple of hours' drive, you'll find several other cities with their own kid-friendly holiday events worth the trip.

Portsmouth, New Hampshire — 1 Hour from Boston

In downtown Portsmouth, enjoy seasonal ice skating at the Portsmouth Outdoor Skating Rink, a festive hub for families with holiday music, lights, and open skate sessions in the heart of the city. You can also join the Santa Claus Shuffle, a festive holiday run through Portsmouth that brings the community together in costume for a cheerful seasonal race supporting local causes.

Cape Cod, Massachusetts — 1 Hour 15 Minutes from Boston

Plan Your Complete Boston Christmas Experience

Boston's Christmas attractions and experiences are just one part of the city's incredible holiday season. Explore our guides to Boston Christmas lights, holiday shows and performances, Christmas festivals and parades, and Christmas markets and holiday shopping. Whether you're a local or visiting for the season, our Boston Christmas guide has you covered.