Westbrook

Day Trips

Make the most of your day with our curated plans, packed with Westbrook's hidden gems and unique experiences!

day 1
Beach Day Delight
morning
:

Start your day with a relaxing stroll along Westbrook Town Beach and enjoy the fresh ocean breeze. Grab a light breakfast at a nearby café, savoring local pastries and coffee.

afternoon
:

Spend the afternoon sunbathing or swimming at the beach. Consider renting kayaks for some exciting water activities or just relax with a good book in hand.

evening
:

Wrap up your day with a seaside dinner at one of the local restaurants, enjoying fresh seafood. Take a peaceful walk along the beach while watching the sunset.

day 2
Nature Exploration
morning
:

Begin your morning with a hike at the nearby Hammonasset Beach State Park. The scenic trails will invigorate your spirit as you immerse yourself in nature.

afternoon
:

Pack a picnic lunch to enjoy amidst the beauty of the park. Spend some time birdwatching or exploring the trails for more stunning views.

evening
:

After a day of adventure, unwind with a casual dinner at a local tavern. Enjoy live music or check out any community events happening that night.

day 3
Local Culture Tour
morning
:

Visit the Westbrook Historical Society to learn about the town's rich history. Spend some time exploring local art galleries and shops.

afternoon
:

Enjoy lunch at a local deli, sampling some regional specialties. Continue exploring the cultural attractions, including galleries and artisan stores.

evening
:

Dine at a charming restaurant that features local cuisine. Consider attending any local theater or live music events for added entertainment.

day 4
Shopping and Dining
morning
:

Start your day with a hearty breakfast at a local diner. Following breakfast, explore the unique shops in the Westbrook Center.

afternoon
:

Enjoy lunch at an outdoor café while people-watching. Visit nearby boutiques for some souvenir shopping or find local handmade goods.

evening
:

End the day with dinner at a restaurant known for its eclectic menu. Explore nearby seafood shacks for a casual, fun dining experience.

day 5
Sailing Adventure
morning
:

Kick off the day with breakfast at home or a nearby eatery before heading to the marina. Join a sailing tour on the beautiful Connecticut shoreline.

afternoon
:

Sail the waters and keep an eye out for local marine life during your adventure. Stop for a packed lunch onboard and enjoy the views.

evening
:

Return to shore for a sunset dinner at a waterfront restaurant. Share tales of your adventure and enjoy the sound of waves crashing nearby.

day 6
Fishing Excursion
morning
:

Begin with an early breakfast before gearing up for a day of fishing at Westbrook's shoreline. Rent fishing equipment if needed and head to your chosen spot.

afternoon
:

Spend your afternoon casting lines and enjoying the peacefulness of the sea. Share a casual picnic lunch on the beach between fishing sessions.

evening
:

Finish off your day by cooking your catch back at your accommodation or taking it to a restaurant that offers cooking services. Reflect on a successful day under the stars.

day 7
Dog-Friendly Day
morning
:

Start the day with a dog-friendly breakfast at a pet-friendly café. Take a morning walk at a local dog park to let your pooch stretch and play.

afternoon
:

Spend time at the beach where dogs are allowed to romp and play. Enjoy a packed lunch on the beach while your dog plays in the water.

evening
:

Head to a pet-friendly restaurant for dinner and enjoy some bites while your dog relaxes by your side. Cap the night with a stroll along Westbrook's scenic waterfront.

day 8
Active Recreation
morning
:

Fuel up with breakfast before renting bicycles to explore the local trails. Cycling is a great way to see Westbrook’s scenic views up close.

afternoon
:

Break for lunch at a picnic spot or local café. Continue biking or stop to hike some trails for more exploration.

evening
:

Return your bikes and reflect on the adventures of the day. Enjoy casual dinner at a burger joint or grill to satisfy your hunger.

day 9
Fireworks & Festivals
morning
:

Ease into your day with brunch at a local favorite spot. Check local event schedules for any festivals or markets happening in town.

afternoon
:

After brunch, spend your afternoon browsing vendor stalls or enjoying various festival activities. Participate in local games and events if available.

evening
:

Conclude your festive day with a community BBQ or food trucks. Enjoy a spectacular fireworks show to cap off the evening under the stars.

day 10
Wellness Retreat
morning
:

Start your morning with a yoga session at a peaceful studio, refreshing your mind and body. Follow up with a nutritious breakfast at a health-focused café.

afternoon
:

Engage in a spa treatment or massage to unwind thoroughly. Consider taking a mindfulness walk along the beach during the afternoon sun.

evening
:

Enjoy a calming dinner packed with healthy options. Spend the evening reflecting on your rejuvenated spirit while enjoying a quiet night stroll.

Discover Westbrook

Read more in our Westbrook 2024 Travel Guide.

Westbrook Travel Guide