5 Fun Gillette Castle Day Trip Ideas
Note: Some of the links in this post may be affiliate links. This means if you click on the link and purchase the item, I will receive a commission. More details are here.
Gillette Castle is one of my favorite unique places in Connecticut! I’ve seen a lot of questions on social media asking about places to eat lunch or other things to do nearby, so I came up with a few day trip ideas. There’s actually a ton of stuff to do in the area!
Keep reading for tips and some fun day trip ideas around Gillette Castle.
Important Tips
These itineraries include some or all meals. You can omit meals or activities if you want a more leisurely day, of course!
Depending on which trip you take, you may cross the Connecticut River twice. I highly recommend getting across the scenic way! I think it adds to the experience to take the Chester–Hadlyme Ferry one way, and the East Haddam Swing Bridge the other way.
➡️ Read important Gillette Castle ferry details and hours in my full guide.
But you can also opt to go the most direct route, especially if you’re short on time.
With all these trips, I highly recommend taking a tour of the interior of the castle. This is what makes the visit in my opinion. In 2026 the castle interior is open daily 10–4 (last tour entry) from Memorial Day weekend through Labor Day, then weekends and holidays only from Labor Day through Indigenous Peoples Day (Columbus Day).
🎟️ Details and tickets here.
The tours are self-guided and docents are stationed throughout the castle to share details. They have timed entry every 15 minutes, and it’s a good idea to buy your tickets ahead of time online as they may sell out on busy days (even the morning of should be fine in my experience). It takes about an hour to go through. Overall, you may plan to spend about 1–3 hours at the castle depending on what you want to do besides the castle tour, such as hiking trails or having a picnic.
Lastly, be sure to check all the hours for the places you will visit before going. Generally, these trips work best Wednesday through Sunday as many of these locations are closed Mondays and Tuesdays. It isn’t feasible for me to include all those details, but I’ve done my best to consider it in building these day trips.
Gillette Castle Day Trips
At a Glance
Trip | Best for | When to go | Approx. Time |
|---|---|---|---|
Castle + Chester | Shops, scenery, the cat theme | Wed–Sun through Labor Day, weekends only through mid-October | 9–10 hrs |
Leisurely Castle Day | Slow pace, hard cider or wine flights | Sat or Sun, Memorial Day–mid-October | 7–8 hrs |
Art + History | Art, gardens, historic houses | Wed–Sun through Labor Day, weekends only through mid-October | 10 hrs |
Lavender + Cider | Yoga in a blooming lavender field, easy summer pace | Saturdays, June–August | 8–10 hrs |
Birdwatching Cruise | Sunset wildlife, photographers, adults | Late Aug–late Sept: Wed–Fri before Labor Day, Sat/Sun after | 8–9 hrs |
1. Castle + Chester Day
Best for: Shops, scenery, and the quirky cat theme
Season: Memorial Day–Indigenous Peoples Day (Columbus Day)
Best days: Wed–Sun (Weekends only after Labor Day)
Book ahead: Castle tour
Time: About 9–10 hours
River crossings: Swing bridge over, ferry back
🗺️ See the map and directions for this trip here. 🗺️
Start the morning by crossing the East Haddam Swing Bridge going toward Goodspeed Opera House. Stop here for photos (see tips below).
Next, head to breakfast at Two Wrasslin’ Cats (9 or 10 AM). I love this stop because it kicks off the cat theme early (Gillette really loved his 15+ cats, which you’ll see on display in numerous ways when you tour the castle).
Enjoy the rest of the morning at Gillette Castle State Park, taking a tour and walking the trails depending on how much time you want to spend there.
Get lunch at nearby Hadlyme Country Market. (Alternatively, you could get lunch to go before heading to Gillette Castle, and enjoy a picnic there.)
Next, take the Chester–Hadlyme Ferry across the river towards Chester. You may be able to get out depending on how the cars are positioned, so you can view the castle from below and take some photos! The castle will be behind you heading this direction.
From here, head to Chester Center to explore the shops, bookstore, galleries, and mill museum (Sat/Sun). This is a small village, so be sure to check whether things are open, especially if you are not visiting on a weekend.
To end the day, enjoy a delicious dinner at Otto and ice cream at Honeycone Craft Ice Cream before heading home. (On Sundays, grab ice cream in the afternoon as Honeycone closes at 6.)
Photo Tip: If you want photos of the Goodspeed Opera House and East Haddam Swing Bridge, you can stop on either side of the bridge. Eagle Landing State Park has a view looking across the river at the opera house and bridge. Or you can park below the opera house in the parking lot on Lumber Yard Road and walk towards Gelston House and the opera house. (🍂 If you’re visiting in the fall, look across the street from the parking lot for a little town scarecrow contest!)
2. Leisurely Castle Day
Best for: A slower pace, hard cider on the lawn
Season: Memorial Day–Indigenous Peoples Day (Columbus Day)
Best days: Sat or Sun*
Book ahead: Castle tour
Time: About 7–8 hours
River crossings: Ferry over, swing bridge back
🗺️ See the map and directions for this trip here. 🗺️
*NOTE: This is best for a weekend if you plan to go to the cidery due to their hours. But you could do it on a weekday if you want to start earlier (the ferry has longer hours during the week) and potentially skip the cider stop.
Start your morning with breakfast at Whistle Stop Cafe in Deep River (we’ve only been once but I’ve read that this small spot gets busy, cash and Venmo only) or Olive Oyl’s in Essex (we’ve heard great things!).
Next, take the Chester–Hadlyme Ferry across the river towards the castle. On weekends, the ferry starts running at 10:30 AM, and on weekdays it starts at 7 AM. So you’ll need to plan accordingly (late breakfast if it’s a weekend). While riding the ferry, you may be able to get out depending on how the cars are positioned, so you can view the castle from below and take some photos.
Enjoy the morning at Gillette Castle State Park, taking a tour and walking the trails depending on how much time you want to spend there.
Pack a lunch for a picnic or get a late lunch at Hadlyme Country Market.
Next, head to the Yankee Cider Taproom to relax on the lawn with a wine or cider flight. This is one of my favorite spots in the area. If you like hard cider, I highly recommend it!
Finish off the day enjoying views of the East Haddam Swing Bridge and Goodspeed Opera House. See the bridge photo tips above!
3. Art + History Day
Best for: Art, gardens, and historic houses
Season: Memorial Day–Indigenous Peoples Day (Columbus Day)
Best days: Wed–Sun (Weekends only after Labor Day)
Book ahead: Castle tour
Time: About 10 hours
River crossings: Cross south on 95, ferry over, swing bridge back
🗺️ See the map and directions for this trip here. 🗺️
Start your day with breakfast at The Hangry Goose in Old Lyme (9 AM), and then head to the Florence Griswold Museum (opens at 10 AM). Wander the grounds and garden, explore the art museum, and take a walk through the house if you have time.
From here, head to Chester to take the Chester–Hadlyme Ferry across the river towards the castle. While riding the ferry, you may be able to get out depending on how the cars are positioned, so you can view the castle from below and take some photos.
This is the scenic route, but you can also head up along the east side of the river for the more direct route!
Head to Hadlyme Country Market for lunch. If you’re not hungry yet, you could take it to go and have a picnic at the castle.
Next, enjoy the afternoon at Gillette Castle State Park, taking a tour and walking the trails depending on how much time you want to spend there. Likely around 2 or 3 PM.
Head up along the river to enjoy views of the East Haddam Swing Bridge and Goodspeed Opera House. See the bridge photo tips above under Trip 1.
Finish off the day with dinner at Gelston House. (I haven’t eaten here yet, but it’s the classic pick next to the opera house.)
Seasonal Gillette Castle Day Trips
4. Lavender + Cider Summer Girls Day (Saturday)
Best for: A girls day when the lavender is blooming
Season: June–August
Best days: Saturday (if you plan to do yoga)
Book ahead: Yoga class + castle tour
Time: About 8–10 hours
River crossings: Ferry over, swing bridge back
🗺️ See the map and directions for this trip here. 🗺️
Kick off the day with yoga in a lavender field at Lavender Pond Farm. They offer this in the summer months starting at 9 AM (book ahead of time). You can spend a little time wandering the lavender fields and stopping into the shop afterwards.
Head to Chester Center to explore the shops, bookstore, galleries, and mill museum.
Enjoy lunch at Otto (opens at 12 on weekends) before going to catch the ferry.
Next, take the Chester–Hadlyme Ferry across the river towards the castle. While riding the ferry, you may be able to get out depending on how the cars are positioned, so you can view the castle from below and take some photos.
Next, enjoy the afternoon at Gillette Castle State Park, taking a tour and walking the trails depending on how much time you want to spend there. Likely around 2 or 3 PM.
Next, head to the Yankee Cider Taproom to relax on the lawn with a wine or cider flight. This is one of my favorite spots in the area. If you like hard cider, I highly recommend it!
Finish off the day enjoying views of the East Haddam Swing Bridge and Goodspeed Opera House. Want photos here? Head to the tips under Trip 1 for info about where to park.
5. Birdwatching in August or September
Best for: Sunset wildlife, photographers, adults
Season: Late August–late September
Best days: Wed–Fri before Labor Day, Sat/Sun after (if going inside the castle)
Book ahead: Cruise (weeks out) + castle tour
Time: About 8–9 hours
River crossings: Ferry back from castle towards Chester/Essex
🗺️ See the map and directions for this trip here. 🗺️
Today starts a little later since it goes into the evening with a boat ride to see the tree swallows at one of their largest migration roosting sites on Goose Island. The season for this is late August through September (peaking in mid-September).
Start the day with lunch at Gelston House or Two Wrasslin’ Cats.
Next, enjoy the afternoon at Gillette Castle State Park, taking a tour and walking the trails depending on how much time you want to spend there.
Next, take the Chester–Hadlyme Ferry across the river towards Chester. You may be able to get out depending on how the cars are positioned, so you can view the castle from below and take some photos! The castle will be behind you heading this direction. On weekends, leave plenty of buffer for the ferry since service ends at 5 PM.
You should have some time to explore the charming Essex Village. Wander Main Street and admire the historical houses, stop into some shops, or relax in the town green (it’s not a typical central town green and feels more like a park, but charming nonetheless!).
Get dinner in Essex. For something quick and inexpensive, I’ve enjoyed Privateers Pizza a few times. Or you can plan ahead to bring a picnic aboard the boat trip.
Note that departure time for boat trips gets earlier as you get later into the season, so you will have less time for wandering or dinner in September than if this is an August trip.
Finish off the evening with a beautiful sunset cruise to see the tree swallows coming in to roost. (MUST book well in advance.)
🐦⬛ There are several tour providers (including human-powered paddling trips), and they usually sell out early in the season. The one I went on was CT River Quest (with naturalist Cathy on board) from the Connecticut River Museum in Essex.
Build Your Own Gillette Castle Day Trip
You can absolutely mix and match these activities to build your own adventure! There are various options for meals and activities to help you plan your day.
Check out the map below and read more about things to do near Gillette Castle here.
What are your favorite things to do on a Gillette Castle day trip? Is there anything else you’d recommend close by?