Premium Cannabis Delivered to Great Barrington
Great Barrington's trusted cannabis delivery service. Licensed, discreet, and fast — with 40+ premium Massachusetts brands delivered straight to your door, from Main Street and the Mahaiwe to Housatonic village, Lake Mansfield, and the foot of Monument Mountain.
Serving Great Barrington
Fast, Discreet Delivery
Residential addresses, Airbnbs & more across the Southern Berkshires
Flexible Delivery Windows
Schedule when it works for you
Great Barrington Delivery
Birthplace of W.E.B. Du Bois — Heart of the Southern Berkshires
Pineapple Express delivers across Great Barrington and the Southern Berkshires. This is the town where W.E.B. Du Bois grew up, where the first electric street lights in the country flickered on in 1886, and where Main Street still draws people from three states. From the Mahaiwe and the shops downtown to Housatonic village, Lake Mansfield, and the trails up Monument Mountain, we're proud to bring it the highest-quality cannabis products.
Downtown to the Villages
We cover all of Great Barrington — Main Street, Housatonic, Van Deusenville, Risingdale, and the roads out toward Butternut and Monument Mountain.
Home & Airbnb Delivery
We deliver to residential addresses, vacation rentals, and Airbnbs throughout Great Barrington. Residential addresses only — we can't deliver to hotel or inn rooms.
100% Discreet
Unmarked vehicles, plain packaging, and plain-clothed drivers. Free delivery with minimum order — small fee under the minimum. Waived for subscribers, Party Packs, and CannaCatering.
Cash, Debit, Aeropay or Straddle
Pay with cash or debit at the door, or ACH through Aeropay or Straddle. Easy, flexible payment options.
ID Verified at the Door
We verify ID at every delivery. 21+ only, always. State-compliant every step of the way.
Delivery Zone
Great Barrington
Berkshire County, MA · 413 Area Code
How It Works
Three Simple Steps
Getting premium cannabis delivered to your Great Barrington address is easier than ever.
Browse Our Menu
Explore our curated selection of premium flower, edibles, concentrates, topicals, and more from Massachusetts' top brands.
- 40+ partner brands
- New brands added often & restocked regularly
- Detailed product descriptions
- Filter by type, brand, or effect
Place Your Order
Select your products, choose your delivery window, and pay with cash, debit at the door, or ACH through Aeropay or Straddle. It's that simple.
- Flexible delivery windows
- Cash, debit, Aeropay or Straddle
- Real-time order tracking
- Earn loyalty points automatically
Get It Delivered
Our driver arrives in an unmarked vehicle with plain packaging. Upload your ID before delivery — quick, required by state law, and never shared.
- Easy ID upload — never shared
- Unmarked vehicles & plain-clothed drivers
- Plain packaging always
- Quick verification at the door
What We Offer
More Than Just Delivery
Standard Delivery
Browse our full menu and get premium cannabis delivered across Great Barrington. Discreet, fast, and fully licensed. Free with minimum order — small fee under the minimum, waived on select orders.
CannaCrates
Subscription boxes with rotating products delivered monthly, biweekly, or weekly — customized to your preferences. Free delivery included.
CannaCatering
Chef-sourced recipes and cannabis-infused culinary products for your Great Barrington events. Elevate your next gathering. Free delivery.
Party Packs
Multi-guest delivery packages for 21+ events. Order in advance and let us handle the rest. Great for Berkshires weekends and rental stays. Free delivery.
Loyalty Program
Earn points on every purchase. Stack rewards and unlock exclusive deals as a valued Pineapple Express customer in Great Barrington.
Referral Credit
Share the love — get $10 credit for you and your friend when they place their first order. Share with Great Barrington friends today.
Our Partners
Carrying the Best in Cannabis
40+ of Massachusetts' finest cultivators and producers, all available for Great Barrington delivery.
Featuring 40+ partner brands — all available for delivery to Great Barrington, MA
Customer Reviews
What Great Barrington Is Saying
Real reviews from real customers across the Berkshires.
“Hands-down the easiest cannabis delivery I've used. The selection is fantastic and the driver was on time and super professional. Couldn't ask for more.”
Hannah R.
Downtown Great Barrington
“I subscribe to the CannaCrate and look forward to it every month. Fresh products, free delivery, and consistently great quality. Highly recommend to anyone in Great Barrington.”
Miles J.
Housatonic, Great Barrington
“Discreet, friendly, and fast. The whole process was smooth from ordering to delivery. I'll be a regular customer for sure.”
Sonia V.
Lake Mansfield, Great Barrington
FAQ
Common Questions
Everything you need to know about ordering cannabis delivery in Great Barrington, MA.
QIs delivery more expensive than a retail store?
Our prices are competitive with retail dispensaries. Delivery is free with a minimum order, with a small fee for orders under the minimum — and always waived for subscribers, Party Packs, and CannaCatering orders. No hidden fees.
QWhat's my daily purchase limit?
Massachusetts law sets limits per transaction. Our team can help you understand your daily limit and make the most of your purchase within legal guidelines.
QWhat payment types do you accept?
We accept cash and debit at the door, plus ACH payments through our partners Aeropay and Straddle — secure, bank-linked options. No credit cards at this time.
QWhat ID do you accept?
Any valid, government-issued photo ID showing you are 21 or older: driver's license, state ID, or passport. Your ID is checked at every delivery.
QDo you deliver to Housatonic and the outer villages?
Yes — we deliver across all of Great Barrington, including the Housatonic, Van Deusenville, and Risingdale villages, plus the roads out toward Monument Mountain and Butternut. If you're not sure your address is in our zone, give us a call and we'll confirm it.
QDo you deliver to Airbnbs and vacation rentals in Great Barrington?
Yes! The Berkshires draw a lot of weekenders, and we deliver to residential addresses including Airbnbs and vacation rentals. Just provide the full address and we'll confirm it falls within our delivery zone. Note that we cannot deliver to hotel or inn rooms — delivery must be to a residential address.
QHow discreet is your delivery?
Extremely. We use unmarked vehicles, plain packaging, and plain-clothed drivers. There's nothing to identify us as a cannabis delivery service from the outside.
QWhat are the taxes on my order?
Massachusetts cannabis is subject to a 10.75% excise tax, 6.25% sales tax, and 3% local tax — 20% total. Taxes are included in product pricing.
QWhat if I didn't receive something I ordered?
Contact us immediately at (413) 277-0277 or kaily@pineappleexpressma.com. We'll make it right. Customer satisfaction is our priority on every Great Barrington delivery.
Ready to Order in Great Barrington?
Browse our full menu of 40+ premium Massachusetts brands and get delivered to your door today. Earn loyalty points on every purchase and enjoy discreet, licensed delivery across the Berkshires.