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Holliston MA Adventure 5 Days Itinerary
Last updated: 2024 Jun 26Exploring Holliston Charm
Morning
Start your day with a visit to the iconic Holliston Historical Society. This site offers a deep dive into the rich history of Holliston and its surrounding areas. The exhibits are well-curated and provide an excellent overview of the town's past. Afterward, enjoy a relaxing stroll through Goodwill Park, where you can take in the natural beauty and perhaps even spot some local wildlife.
Afternoon
In the afternoon, embark on Christmas by Candlelight at Old Sturbridge Village. This tour will transport you back in time to experience an old-fashioned Christmas celebration. The village is beautifully decorated, and you'll get to participate in various holiday activities that are both fun and educational.
Evening
For dinner, head over to Bertucci's Italian Restaurant for some delicious Italian cuisine. Afterward, unwind with a drink at The Rail Trail Flatbread Co, known for its cozy atmosphere and extensive drink menu.
Bedtime
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Mystery and History in Dedham
Morning
Begin your day with a hearty breakfast at The Friendly Toast, a popular spot known for its eclectic menu and vibrant atmosphere. Then make your way to Dedham Square for some shopping and sightseeing.
Afternoon
In the afternoon, challenge yourself with The Escape Game Dedham: 60-Minute Adventures at Legacy Place. This escape room experience is perfect for those who love puzzles and adventure. It's a thrilling way to spend an hour as you work together to solve clues and escape before time runs out.
Evening
For dinner, dine at Legal C Bar, which offers fresh seafood dishes that are sure to delight your taste buds. End your evening with a visit to Isabella Stewart Gardner Museum Cafe for some coffee or dessert.
Bedtime
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Scavenger Hunt on Nantucket Island
Morning
Catch an early ferry from Hyannis Port to Nantucket Island. Once you arrive, start your day with breakfast at Black-Eyed Susan's, a beloved local eatery known for its hearty morning meals.
Afternoon
Spend your afternoon on Nantucket: Private Scavenger Hunts. This unique tour will have you exploring the island while solving clues and learning about Nantucket's history along the way. It's a fun activity that's perfect for families or groups of friends.
Evening
After completing the scavenger hunt, enjoy dinner at Galley Beach Restaurant, which offers stunning ocean views and delicious seafood dishes. Conclude your day with drinks at The Nautilus, a trendy bar known for its creative cocktails.
Bedtime
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Cultural Immersion in Holliston
Morning
Begin your day with a visit to the Holliston Public Library. This charming library is not only a great place to relax with a book but also offers various community events and exhibitions that showcase local culture and history. Afterward, take a leisurely walk through Blair Square, where you can enjoy the quaint shops and cafes.
Afternoon
In the afternoon, join Christmas by Candlelight at Old Sturbridge Village once again if you missed it earlier or want to experience it anew. The festive atmosphere and historical reenactments make it a delightful way to spend your afternoon.
Evening
For dinner, head over to Bazels Sub & Pizza for some delicious comfort food. Afterward, unwind with a drink at The Central House Tavern, known for its friendly atmosphere and wide selection of beverages.
Bedtime
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Final Day of Fun in Dedham
Morning
The Escape Game Dedham: 60-Minute Adventures at Legacy Place awaits you for another round of thrilling escape room fun. Test your wits and teamwork skills as you tackle new challenges.
Afternoon
Nantucket: Private Scavenger Hunts offers another exciting scavenger hunt experience if you're up for more adventure. Alternatively, explore Dedham's historic sites such as the Fairbanks House, the oldest timber-frame house in North America.
Evening
Dedham House of Pizza is a great spot for dinner with its tasty pizzas and casual dining atmosphere. Conclude your trip with drinks at Punch Bowl, a cozy bar perfect for relaxing after an eventful day.
Bedtime
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