Massachusetts Berkshires to Beaches Adventure

Massachusetts Berkshires to Beaches Adventure

Mountain Trout Streams, Warm Water Predators, and Saltwater Flats.

Starting along the Appalachian trail in the Berkshires of Western MA we will fish for trout in small mountain streams. As we make our way east towards the ocean the mountains flatten and the rivers widen. As the rivers get bigger so do the fish in them. During an overnight canoe trip on the Housatonic River, we will observe as the trout make way for aggressive smallmouth and predatory pike. Eventually, our journey east will bring us to the ocean. Flats fishing may not be the first thing that comes to mind when you think of Cape Cod, but what looks like a bottomless ocean at high tide reveal a maze of rivers and flats as the tides recede. Our trip coincides perfectly with the ideal time of year to target Striped Bass as they search the flats looking for crabs and sand eels. For three days we will camp on the Cape with easy access to the Brewster and Chatham Flats where we will hunt for stripers with the help of a local guide Patrick from Cape Cod on the Fly. The final two nights of the trip, we will head to the North Shore where we will charter boats for our final fishing adventure. We will relive it all together during our final banquet dinner before we head home the next day.

Upcoming Trips

Dates Cost Arrive/Depart Location
Jun 18 - Jul 01, 2021


Boston, MA
Entering 7th Grade
Entering 8th Grade
Entering 9th Grade
Entering 10th Grade
Community Service
5 Hours
What to Bring

We have put together a list of all that you will need for a successful and comfortable expedition. We offer a rental program for most of the big ticket items like fly rods, reels, sleeping bags, etc..

Day 1-4

After arriving in Boston we will head to Western MA where we will kick off our trip by dialing in our fly fishing skills while wading for some trout and smallmouth bass. 

Day 5-7

A 3-day canoe trip starting in Western Massachusetts provides amazing diversity as we follow the river east. Trout, Smallmouth, and large predatory Pike all call the river home. 

Day 8-12

After loading up our canoes we will head further east to Cape Cod. The flats of Cape Cod create some of the best opportunities to wade fish for Striped Bass. Our campground on the Cape is central to two of the best flats. For three days we will wade the flats with local guide Patrick from Cape Cod on the Fly. After one more morning fishing on the Cape, we will make the drive to our last campground on the "North Shore". 

Day 13-14

The last full day of the trip will be spent putting our new skills to use on a guided saltwater charter. With multiple boats and some of the best local captains, we will divide up in search of some of the huge stripers that pass through this area during this time of year. After a full day on the water, we will enjoy our final feast together as a group before departing from Boston the next morning. 

  • Brown, Brook, and Rainbow Trout
  • Smallmouth Bass
  • Largemouth Bass
  • Northern Pike
  • Striped Bass
  • Blue Fish 


The Massachusettes Berkshire to Beaches Adventure begins and ends at Boston Logan International. Participants can fly to/from the airport on arrival/departure day or be dropped off/picked up by a parent/guardian. Please plan to arrive before 3 pm. On the last day of the trip flights that depart before 2 pm are ideal. We will meet unaccompanied minors at their gate. Participants flying as an adult should follow signs to the baggage claim area. Their trip director will meet you there. On departure day, your trip leaders will help you get checked in and wait with the group until the last participant's flight leaves the ground.

Do I need to have fly fishing experience? 

Our Adventures are made up of students ranging in experience from total beginner to expert. Regardless of your skill level, your guides, along with a variety of water fished, will make you a more confident and independent angler. 

Do I need my own fishing equipment?

Students are responsible for their own fly rod, reel, line, and a few other personal fishing items. Please contact us for a full packing list. Don’t have your own gear? Not a problem. We have top-quality Orvis rods and reels available to rent.

What other equipment will I need?

We will send you a full packing list if you are interested in signing up for one of our Adventure Academies. Group gear such as tents, stoves, etc., is all provided by LFFE. Personal gear such as sleeping bags and backpacks are all available to rent.

Ready to Enroll?

Click "Enroll Now" or give us a call to get started. You can also send us an email at [email protected].

If you have any questions you can Request Information and we will contact you soon with answers.

Lillard Fly Fishing Expeditions was started in 2010 as a graduate thesis for my Master's Degree in Environmental Conservation Education at NYU. The operating premise was simple - by coupling amazing wilderness fly fishing camps for teens with environmental education and service learning we can help inspire future generations of fly fishing conservationists. We have been growing our unique list of trips and experiences ever since.

When it comes to choosing a summer program for your teen the options are endless. For the teen who loves to fish, be outside, and has a strong sense of adventure we have made the choice easy. We are the leader in teen fly fishing adventures and are dedicated to providing the best backcountry fly fishing experience with opportunities for teens to engage in leadership training, community service, and backcountry camping.


Will Lillard signature

Will Lillard, Founder/Director/Guide

Contact Us

[email protected]

Lillard Fly Fishing Expeditions
2540 King Road
Pisgah Forest, NC 28768

(828) 577-8204