Berkshire to Beaches Expedition

Berkshire to Beaches Expedition

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

The Berkshires are the perfect destination to bring your trout fishing skills to the next level. As we make our way back east, the mountains flatten, and the rivers widen. As the rivers get bigger, so do the fish in them. We will observe as the trout make way for aggressive smallmouth and predatory pike during an overnight canoe trip on the Housatonic River. 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 reveals a maze of rivers and flats as the tide recedes. 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. On the final two nights of the trip, we will head to the North Shore. Our last fishing adventure starts early that morning when 3 of the best local captains pick us up from our campground marina to fish for big stripers and blues on fly and light tackle. That night, we relive it all together during our banquet dinner before heading home the next day.

Upcoming Trips

Dates Cost Arrive/Depart Location
Jun 18 - Jul 01, 2024


Boston, MA
Entering 9th Grade
Entering 10th Grade
Entering 11th Grade
Entering 12th 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.. If you are already enrolled, you can rent gear by logging into your account at: and navigating to Forms & Documents —> Rental Options.

Day 1-3

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 4-6

As we start to move toward the coast, we will set up camp on a section of river with even more variety. It is possible to catch trout, smallmouth, and pike wading in front of the campsite, but mastering the art of fly fishing in a canoe will significantly increase our success. With our fleet of canoes, we can fish multiple sections up and downstream of camp. 

Day 7-10

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. We will wade the flats with the help of local guide Patrick from Cape Cod on the Fly for three days. After our final morning spent fishing on the Cape, we will make the drive to our last campground on the "North Shore." 

Day 11-12

We will spend the last full day of the trip putting our new skills to use on a guided saltwater charter. The best local captains will pick us up right from our campground, and we will split up in search of some of the giant stripers that pass through this area during this time of year. Then, after a memorable day on the water, we will enjoy our final feast together as a group before departing from Boston the following day. 

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


The Massachusettes Berkshire to Beaches Expedition 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 Expeditions are made up of students ranging in experience from excited beginners to seasoned experts. Regardless of your skill level, your guides will work with you to 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.

This was my second year of Lillard trips and I could not recommend them more. Calling them amazing would be an undersell. LFFE is an incredible company and my biggest regret is not starting with them sooner.

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