BIG NEWS: Trailhead Printing Just Launched a Fully Custom Online Apparel Ordering Experience!

February 13, 2026

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Trailhead Printing has always been your trusted, locally-owned print shop right here in Simsbury. We’ve built our reputation on relationships, quality, and affordability.


Now? We’ve taken that same local care and brought it online in a fully custom ordering experience that puts you in control.



Whether you’re a small business, school, nonprofit, sports team, or just printing one shirt for yourself — you can now customize, quote, and order online in minutes.


And yes… you can still pick it up right here at your favorite local print shop.

Custom business cards at Trailhead Printing

Upload Your Design & Customize Everything

Our new portal lets you:


  • Upload your artwork (PNG, JPG, PDF)
  • Choose placement (front, back, sleeve)
  • Adjust print size
  • Select garment styles and colors
  • Choose your decoration method
  • See a real-time ballpark estimate
  • Submit your order instantly



No waiting. No guesswork. No complicated back-and-forth just to get started.

Choose the Perfect Garment

Browse dozens of apparel options and filter by brand, color, size, or style. From performance tees to long sleeves and team gear, everything is right at your fingertips.


Need moisture-wicking athletic wear for a team?

Outfitting your staff with branded polos?
Ordering event shirts for a fundraiser?



You can do it all online — whenever it’s convenient for you.

Online custom apparel ordering portal showing garment selection, design upload, decoration method options, size selection, and instant price estimate.

Pick Your Decoration Method

We make it simple to choose what works best for your design:


DTF (Direct-to-Film) Printing


  • Full color & photo quality
  • Great for detailed artwork
  • No minimum order
  • Fast turnaround


Perfect for bold graphics, gradients, and smaller runs.


Embroidery


  • Premium, professional look
  • Extremely durable
  • Great for logos and text
  • Ideal for uniforms and business apparel


Not sure which is best? The portal helps guide you — and we’re always here if you have questions.

Trailhead Printing custom apparel portal with design upload, garment selection, and instant quote summary.

Instant Pricing

One of the most exciting features?


You’ll see an instant estimate summary as you build your order.


  • Garment cost
  • Decoration fee
  • Small order adjustments (if applicable)
  • Estimated total


It’s transparent, simple, and built to save you time.



Once submitted, our team reviews your artwork and sends a confirmed quote before anything goes to print. We’re still local. We still double-check everything. We just made it easier to start.

What This Means for Local Customers

If you’ve ever:


  • Needed a last-minute team shirt
  • Wanted one custom gift
  • Been unsure how to start a print order
  • Didn’t want to email back and forth for pricing


This is for you. You can now build your project on your own time — whether that’s 10pm on the couch or during your lunch break.



And when it’s ready? You can pick it up right here in town.

What This Means for Local Businesses

For small businesses, contractors, schools, restaurants, gyms, and nonprofits — this is a game changer.


  • Quickly reorder staff shirts
  • Try new logo placements
  • Compare embroidery vs. print
  • Build event merchandise
  • Submit group orders
  • Plan seasonal apparel drops


All without waiting days for a quote just to explore options.



It’s the convenience of a national online platform — backed by a local team that knows your name.

Ready to Try It?

Start customizing today at: https://order.trailheadprinting.com/apparel


  1. Upload your design.
  2. Build your order.
  3. Get your estimate.
  4. Pick up locally.


We’re proud of this upgrade — and even more excited to see what our community creates with it.

If you try it out, let us know what you think. We built this for YOU. 💚

Questions? Call (860) 248-6113 or email sales@trailheadprinting.com today!

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Simsbury, Connecticut, is more than just a picturesque town; it's a vibrant community with a strong commitment to supporting local businesses. Whether you're a budding entrepreneur or an established enterprise looking to grow, knowing where to find key resources can make all the difference. At Trailhead Printing , we're proud to be part of the Simsbury business fabric, and we want to help our fellow local businesses thrive. Let's dive into some essential resources that can help your Simsbury business succeed! 1. Granby-Simsbury Chamber of Commerce: Your Local Advocate The Granby-Simsbury Chamber of Commerce is often the first stop for businesses looking to connect and grow within the community. They offer: Networking Opportunities: Regular events, mixers, and forums to meet other local business owners and potential clients. Business Advocacy: A collective voice to represent local business interests to town government and state agencies. Resource Referrals: Guidance on local regulations, economic development programs, and other essential services. Becoming a member is a fantastic way to integrate your business into the local economy and stay informed about important town initiatives. 2. Town of Simsbury Economic Development The Town of Simsbury's Economic Development Department is dedicated to fostering a healthy and growing business environment. They can provide: Guidance for New Businesses: Assistance with understanding local zoning, permitting, and regulatory processes. Data and Demographics: Information on Simsbury's population, consumer base, and market trends to help you make informed decisions. Site Selection Support: Help in finding appropriate locations for your business within the town. Their goal is to ensure that businesses have the support they need to establish, operate, and expand successfully in Simsbury. 3. Understanding Local Regulations: Temporary Sign Permits One often-overlooked but crucial aspect of local business operations is understanding signage regulations. Effective signage is vital for visibility, but it must comply with town ordinances. For businesses looking to use temporary signs to promote events, sales, or seasonal offerings – such as A-frame signs or yard signs – it's important to obtain the necessary permits. These signs are excellent for catching local attention, but the town has rules in place to ensure they are used appropriately and safely. You can find information and the application for a temporary sign permit directly on the Town of Simsbury's website. We highly recommend reviewing this information before deploying any temporary outdoor signage: Link: Town of Simsbury Temporary Sign Permit Application Town of Simsbury Temporary Sign Permit Application Pro Tip: At Trailhead Printing , we specialize in creating durable and eye-catching A-frame signs and yard signs that meet local specifications. Once you have your permit, we can help you design and print signs that effectively get your message across! Partnering for Success in Simsbury Simsbury offers a wealth of resources designed to help businesses like yours flourish. By leveraging the Chamber of Commerce, the Economic Development Department, and understanding key regulations like temporary sign permits, you can build a stronger, more visible, and more successful business. At Trailhead Printing, we're here to support your visual communication needs, from brochures and business cards to those essential temporary signs. Let's grow together in Simsbury!
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