Your complete guide to holiday shopping, festive events, and seasonal magic in downtown Salem
The leaves have fallen, the jack-o’-lanterns are packed away, and something new is stirring in downtown Salem. This isn’t just another holiday season—it’s the inaugural year of Holiday Happenings, your one-stop guide to everything that makes Salem magical from late November through New Year’s.
Think of it as Salem’s winter answer to Haunted Happenings: a curated collection of events, experiences, shopping, and seasonal charm that transforms our historic downtown into a winter wonderland.
What is Holiday Happenings?
Holiday Happenings brings together everything you love about Salem during the holidays in one easy-to-find place:
✨ Signature Community Events – From the Tree Lighting to Wassail Weekend
🛍️ Downtown Shopping Guide – Discover unique gifts at local businesses
🎄 Holiday Experiences – Special tours, activities, and seasonal magic
🗓️ Unified Calendar – Never miss a holiday happening again
📍 Easy Navigation – Find parking, hours, and insider tips
It’s your personal holiday concierge for Salem, making it easier than ever to experience the season’s best.
The Events You’ll Love
🎅 Tree Lighting & Santa’s Arrival – November 28th
Kick off the season with Salem’s most beloved tradition! Santa arrives via the Salem Fire Department (yes, really) at the historic Hawthorne Hotel, then leads a magical lantern-lit procession down Essex Street to Lappin Park. Bring the kids, grab some hot cocoa, and watch as our community lights up the night with our tree.
Where: Salem Common & Lappin Park
When: 6:00 PM
Cost: FREE!
Bring: Your lanterns and holiday spirit.
The Johnson-Mitchell Family of Middleton generously donated this year’s tree. Costumed carolers from History Alive will provide seasonal serenades throughout the evening. Organizers recommend arriving at Salem Common by 5:45 p.m. to catch Santa’s dramatic rooftop arrival.
Important: This event is rain or shine and completely free—no tickets required! Be aware of scam duplicate events that may ask you to purchase tickets.
🛍️ Small Business Saturday – November 29th
The day after Tree Lighting, keep the momentum going with Small Business Saturday! Kick off your holiday shopping with exclusive deals and promotions from over 50 participating downtown businesses. Pick up your Holiday Passport and start earning rewards as you shop local.
This is your chance to find unique gifts while supporting the neighbors who make Salem special. Many businesses will feature special promotions, extended hours, and exclusive Small Business Saturday offerings.
Special Event: Small Business Saturday Artisan Pop-Up at Jenni Stuart Fine Jewelry (79 Washington Street, 5:00-9:00 PM) featuring local makers including Salem Style crochet accessories, Love Letter Confections artisanal chocolates, Tim McAuliffe Pottery, and more. Discover handcrafted treasures while experiencing Jenni Stuart’s signature permanent bracelets in solid 14k gold!
🍷 Wassail Weekend – December 13-14
Downtown Salem gets extra festive with special promotions, roaming carolers, and seasonal cheer throughout the shops and restaurants. It’s the perfect weekend to check everyone off your gift list while soaking in the holiday atmosphere. Santa makes appearances on Sunday!
Where: Throughout Downtown Salem
When: All weekend
What to Expect: Shopping specials, live music, festive vibes
Grab brunch at one of Salem’s many fine local eateries, then hit the pavement for special promotions and unique finds downtown. Keep your eyes peeled for Santa and roaming carolers on Sunday afternoon!
🪟 Holiday Window Decorating Contest – Starting December 6
Our downtown merchants go all-out, decorating their storefronts in holiday splendor. Stroll through downtown and admire the creativity as local businesses transform their windows into festive displays. Look for the white Holiday Happenings decals to find participating businesses.
This beloved Salem Main Streets tradition encourages businesses to showcase their holiday spirit and add to the festive atmosphere throughout downtown. From classic holiday scenes to uniquely Salem-inspired displays, each window tells its own seasonal story.
Interested in participating? Downtown businesses should contact Kylie at Salem Main Streets to join this year’s contest and receive your Holiday Happenings window decal.
🎨 Holiday Workshops & Special Experiences
Holiday Happenings isn’t just about shopping and events—it’s about creating memories! Throughout the season, discover hands-on workshops and unique experiences:
Create Your Own Holiday Ornament Workshop
Design and craft personalized ornaments to treasure for years to come or give as heartfelt gifts. Multiple dates and locations throughout the season.
Build-a-Snowman in the Snow Room
Experience the magic of winter indoors! Perfect for families and those dreaming of a white Christmas.
Festive Dining Experiences
Many downtown restaurants offer special holiday menus, seasonal cocktails, and cozy atmospheres that are perfect for celebrations with friends and family.
Holiday Ghost Tours & Historic Walks
See Salem through a different lens with specialty walking tours that blend the city’s rich history with seasonal storytelling. Several tour companies offer holiday-themed experiences throughout December.
Holiday Happenings also connects you to other magical Salem experiences:
Christmas in Salem Historic House Tours – Explore beautifully decorated historic homes throughout different Salem neighborhoods (first weekend in December, presented by Historic Salem, Inc.)
Strippin’ Around the Christmas Tree – An adults-only burlesque celebration with yuletide tributes to favorite holiday characters and movies, presented by Siren of the Circle
Special Holiday Performances – Live music, theatrical productions, and seasonal entertainment at venues throughout the city
Salem Arts Association Annual Holiday Market – Discover unique handmade gifts from local artisans and crafters
Shop Local, Shop Special
Here’s the thing about shopping in downtown Salem during the holidays: you’re not just buying gifts—you’re having an experience.
What You’ll Find:
- One-of-a-Kind Gifts – Custom jewelry, handmade crafts, local art, vintage finds
- Unique Experiences – Ghost tours with a holiday twist, historic walks, magical shops
- Personal Service – Real people who know their products and love helping you find the perfect gift
- No Big Box Sameness – Every store has its own personality and carefully curated selection
Plus, when you shop downtown Salem, you’re supporting the neighbors who sponsor your kids’ teams, volunteer at community events, and make our city vibrant year-round. That’s pretty special.
The Holiday Happenings Website: Your New Best Friend
We’ve created a comprehensive digital guide that makes holiday planning actually enjoyable:
📱 Browse Participating Businesses
Filter by category, location, or item type. Each listing includes photos, hours, special holiday offerings, and what makes them unique.
🗓️ See All Holiday Events
One calendar with some of the best holiday events in Salem. No more hunting across multiple websites.
🎁 Get Insider Tips
Where to park, when to visit for smaller crowds, which restaurants take reservations, and more local knowledge.
🛍️ Plan Your Perfect Day
Sample itineraries help you make the most of your downtown visit—whether you’ve got two hours or a full day.
Why This Year Feels Different
If you’ve been to downtown Salem during the holidays before, you know it’s always been charming. But Holiday Happenings brings a new level of coordination and care:
- Better Information – Everything in one place, easy to find
- More Festive Atmosphere – Enhanced decorations, coordinated events
- Unified Marketing – Easier to discover what’s happening
- Business Support – Helping your favorite local shops thrive
It’s the same Salem magic you love, just easier to experience and enjoy.
How to Join the Fun
1. Visit the Website
Visit our directory to explore participating businesses, check out the events calendar, and plan your visit.
2. Mark Your Calendar
Tree Lighting is November 29th—that’s when it all officially kicks off. From there, Wassail Weekend (Dec 14-15) is your next big date.
3. Follow Along
Stay connected on Instagram @salemmainstreets and @creativecollectiveexplores and Facebook for daily inspiration, special promotions, and behind-the-scenes peeks.
4. Shop Early, Shop Local
Beat the rush and support downtown businesses. Many offer custom orders, so the earlier you start, the more options you have.
5. Spread the Word
Share your favorite finds, tag businesses in your posts, and use #HolidayHappenings to show your Salem pride.
Special Experiences to Discover
Beyond traditional shopping, Holiday Happenings connects you to unique seasonal experiences:
- Historic Holiday Tours – See Salem through a different lens with specialty walking tours
- Festive Dining – Seasonal menus and cozy atmospheres at local restaurants
- Live Music & Performances – Carolers, brass bands, and seasonal entertainment
- Photo Opportunities – Beautifully decorated streets perfect for holiday cards
- Gift Wrapping & Consultations – Many businesses offer special holiday services
Making Memories, Not Just Purchases
Here’s what we really hope Holiday Happenings becomes: a tradition.
A tradition of taking the family downtown for Tree Lighting each year. Of doing your holiday shopping on actual streets with actual storefronts instead of scrolling through endless online options and supporting the businesses that make Salem, Salem.
Your presence downtown during the holidays—whether you’re spending money or just soaking in the atmosphere—matters. It keeps our historic district vibrant. It gives local business owners reason to invest in making their shops memorable. It creates the kind of community experiences you can’t get from a shipping box.
This Season, Choose Experience Over Expedience
We know online shopping is easier. You can do it in your pajamas. With two-day shipping. While watching TV.
But here’s what you can’t get online:
- The smell of hot cider from a street vendor
- The sound of carolers on Essex Street
- The help of a local shopkeeper who knows precisely what your impossible-to-buy-for aunt would love
- The memory of your kid’s face when they see Santa arrive on a fire truck
- The satisfaction of checking off your gift list while actually enjoying the process
Those things? They only happen in person, in community, in downtown Salem.
A Word About Small Businesses
We’d be remiss not to mention: your local retailers have had it rough. The pandemic changed shopping habits. Big chains have bigger budgets. Online retail keeps growing.
But these businesses? They’re the reason Salem has character instead of cookie-cutter predictability. They employ your neighbors. They donate to local causes. They make downtown a destination, not just a drive-through.
When you choose to shop local this holiday season, you’re not just buying gifts—you’re voting for the kind of community you want to live in.
Holiday Happenings makes it easier to make that choice.
Get Started This Week
Don’t wait for December to start planning.
- Browse the business directory and start your gift list
- Check out the events calendar and add dates to your phone
- Read about parking options and plan your visit
- Follow along on social media for inspiration and updates
- Sign up for email updates about special promotions and events
The Tree Lighting is on November 29th, but your Holiday Happenings experience can start right now.
Join Us for Salem’s Most Magical Season
This is the first year of Holiday Happenings, and we’re building something special. We’re creating the resource Salem residents and visitors have been asking for: one place to discover everything that makes our holiday season magical.
Will you be part of the story?
Mark your calendar for Tree Lighting on November 29th. Start browsing the website. Follow along on social media. And when you’re ready to start checking names off that gift list, head downtown.
Salem’s holiday magic is waiting.✨🎄🛍️
Holiday Happenings officially launches Friday, November 29th at the Tree Lighting.
Explore businesses, events, and guides. | Follow #salemholidayhappenings
Behind Holiday Happenings
Holiday Happenings is co-organized by Creative Collective and Salem Main Streets, with website support from Jenni Stuart Fine Jewelry and Witch City Walking Tours, and produced in partnership with Destination Salem and the City of Salem.