Middletown

Day Trips

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

day 1
Exploring Historic Center
morning
:

Start your day with a leisurely breakfast at a local café, enjoying freshly brewed coffee and homemade pastries. Afterward, take a stroll through Middletown's historic downtown area, soaking in the charming architecture and vibrant storefronts. Don't miss a visit to the famous Middletown Historical Society to learn about the town's rich past.

afternoon
:

For lunch, head to a popular eatery that serves delicious local cuisine, perhaps trying a classic New England clam chowder. Afterward, visit the nearby museums or art galleries, immersing yourself in the local culture and artistic expressions. Spend some time at the scenic parks, where you can relax and appreciate the beautiful natural surroundings.

evening
:

As the sun sets, enjoy dinner at a waterfront restaurant offering stunning views of the river. After your meal, take a leisurely walk along the riverfront, where you can watch the boats glide by and listen to the sounds of nature. Conclude the day by catching a live performance or local music at a nearby venue.

day 2
Adventures at the Beach
morning
:

Kick off your day with a hearty breakfast at a beachside diner, fueling up for a day of fun in the sun. After breakfast, head to the local beach, where you can enjoy a refreshing swim in the Atlantic Ocean. Spend some time basking in the sun or building sandcastles before the crowds arrive.

afternoon
:

After a morning of beach fun, grab a casual lunch from a nearby beach shack offering fresh seafood and cold drinks. Spend your afternoon engaging in water sports such as paddleboarding or kayaking, exploring the coastline from a unique perspective. Alternatively, you might simply relax with a good book under an umbrella, listening to the sound of the waves.

evening
:

As the day winds down, enjoy a sunset picnic on the beach, complete with local cheeses and wines sourced from nearby vendors. After your meal, take a long, romantic walk along the shore, collecting seashells and enjoying the peaceful atmosphere. Cap off the night with a bonfire, roasting marshmallows while stargazing.

day 3
Mountain Hiking Adventure
morning
:

Start your day early with a nutritious breakfast at your accommodation or a nearby café to fuel your hiking adventure. Pack your gear and drive to the stunning nearby mountains, where you can find trails suited for all skill levels. As you begin your hike, admire the beautiful views of the surrounding nature and breathe in the fresh mountain air.

afternoon
:

After a few hours of hiking, take a break for lunch at a scenic overlook, enjoying a packed meal surrounded by breathtaking views. Continue your hike, perhaps exploring different trails that lead to waterfalls or hidden viewpoints. Keep an eye out for local wildlife as you traverse the trails, making sure to capture the moments with photos.

evening
:

Return to Middletown feeling accomplished and invigorated, and treat yourself to a well-deserved dinner at a cozy restaurant specializing in farm-to-table dishes. Share stories of your adventure with friends or family over a delicious meal. If available, consider attending a local outdoor movie night or community event to unwind.

day 4
Cultural Immersion Day
morning
:

Begin your day with breakfast at a local café known for its artisanal offerings, fueling up for a day of cultural exploration. Visit the local cultural center, where you can participate in workshops showcasing traditional crafts and art forms. Spend the morning learning about the diverse cultures that make up Middletown’s community.

afternoon
:

For lunch, opt for a restaurant that features international cuisine, giving you a taste of the world without leaving town. Afterward, visit a local gallery or museum hosting an exhibition that highlights regional artists and their unique perspectives. Engage with local artists if possible, learning about their creative processes and inspirations.

evening
:

In the evening, attend a cultural festival or live performance that showcases local music, dance, or theater. Enjoy dinner from food vendors offering a variety of dishes, allowing you to sample different flavors. Wrap up the evening by socializing with locals and reflecting on the day’s enriching experiences.

day 5
Nature and Wildlife Exploration
morning
:

Start your day with a breakfast picnic at a local park, where you can enjoy nature while dining al fresco. Afterward, visit a nearby nature reserve or wildlife sanctuary, where you can take guided tours to learn about local flora and fauna. Bring binoculars for birdwatching or simply enjoy the peaceful surroundings.

afternoon
:

For lunch, return to town and grab a bite at a café with outdoor seating, allowing you to soak in the fresh air. Spend your afternoon hiking or biking through scenic trails, with opportunities to take photographs of the stunning landscapes. If you're lucky, you might spot some local wildlife along the way.

evening
:

As the sun sets, participate in a guided evening nature walk that highlights the nocturnal wildlife of the region. Afterward, enjoy dinner at a local farm-to-table restaurant that focuses on seasonal ingredients. Conclude your day with a relaxing evening by a fire pit, sharing stories about your wildlife encounters.

day 6
Local Markets and Shopping
morning
:

Begin your day with a delicious breakfast at a local bakery, sampling fresh breads and pastries. Afterward, head to the Middletown farmers' market, where you can explore stalls filled with fresh produce, homemade goods, and artisan crafts. Take your time chatting with vendors and tasting samples of local delicacies.

afternoon
:

Enjoy a casual lunch at a nearby deli or café, fueling up for an afternoon of shopping. Explore local boutiques, antique stores, and specialty shops, finding unique souvenirs and gifts to take home. Don't forget to visit local artisans' studios, where you can see their work and even purchase some handmade pieces.

evening
:

As the evening approaches, treat yourself to a lovely dinner at a restaurant known for its local fare and cozy ambiance. If available, join a local cooking class or food tour to learn more about the culinary traditions of the area. End your day with a delightful dessert from a nearby ice cream shop or bakery, savoring the flavors of your adventures.

day 7
Historical Landmarks Tour
morning
:

Start your day with breakfast at a charming café, preparing for a day steeped in history. Head out to visit significant historical landmarks in Middletown, such as the Old Jailhouse and the Historic Courthouse, where you can take guided tours to learn about their importance. Immerse yourself in the stories of the past as you explore each site.

afternoon
:

For lunch, enjoy a meal at a historic inn that has preserved its charm over the years. Afterward, continue your exploration by visiting the local cemetery, where you can discover the resting places of notable figures from Middletown's history. Take time to reflect on the stories behind the gravestones and perhaps even do some genealogy research.

evening
:

Wrap up your historical day with dinner at a restaurant that features historical décor and menu items inspired by local traditions. Attend a talk or presentation at the local historical society to learn more about the town's heritage. Finish the evening with a ghost tour that will share spooky tales and legends from Middletown's past.

day 8
Family Fun Day at Amusement Park
morning
:

Kick off your day with breakfast at a family-friendly diner, filled with energizing options for kids and adults alike. After breakfast, head to a nearby amusement park, where excitement and adventure await you. Spend the morning riding thrilling roller coasters and playing games, creating lasting memories.

afternoon
:

Take a break for lunch at the park, enjoying classic amusement park fare like hot dogs and cotton candy. Afterward, explore more attractions, from live shows to fun interactive exhibits that entertain and educate. Make sure to capture plenty of family photos to remember the day.

evening
:

As the day draws to a close, enjoy a final dinner at a themed restaurant that caters to families, complete with a playful atmosphere. Afterward, stick around for the evening parade or fireworks show, a perfect way to conclude your fun-filled day. Head back to your accommodation, reminiscing about all the laughter and joy shared.

day 9
Relaxation and Spa Day
morning
:

Begin your day with a peaceful breakfast at a tranquil café, savoring healthy options to start your relaxation journey. Afterward, head to a local spa for a morning of pampering, indulging in massages and skincare treatments that rejuvenate your body and mind. Take advantage of the spa's amenities, such as saunas or hot tubs, to further enhance your relaxation.

afternoon
:

Enjoy a light lunch at a nearby health-focused restaurant, selecting dishes that nourish the body and continue the wellness theme. Spend your afternoon participating in a yoga or meditation class, finding your center and calming your spirit. Embrace the serene environment as you connect with like-minded individuals in the community.

evening
:

As the sun sets, enjoy a healthy dinner at a local bistro that prioritizes fresh ingredients and wholesome flavors. Consider attending a wellness workshop or seminar in the evening to learn more about self-care practices. Conclude your relaxing day with a quiet walk around a nearby park, reflecting on your experiences and newfound tranquility.

Discover Middletown

Read more in our Middletown 2025 Travel Guide.

Middletown Travel Guide