Experience · Upland

Upland Date Night Escape & Italian

Kick off your evening with an exciting challenge at an escape room, working together to solve puzzles and escape before time runs out. Afterward, unwind and share stories over a delightful Italian dinner at a charming local spot. For a truly relaxed ending, grab an optional nightcap at a nearby pub.

A 4.5-hour Upland evening plan for couples — Experience Machine Escape Rooms, Allegro, Black Watch Pub.

Duration: 4h 30m
Cost: $100–$250
Stops: 3 stops
Walking: Light walking · Total 4.8-mile driving route
Best time: 5:00 – 10:00 PM
Ideal for: Couples · Friends · Adults · Solo

Start Plan

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The plan

1Experience Machine Escape Rooms(1 hr 30 min)→
2Allegro(1 hr 30 min)→
3Black Watch Pub(1 hr 30 min)

Why this plan works

The 3 stops cover about 4.8 miles total, which keeps you in one pocket of Upland instead of crossing town between them. Experience Machine Escape Rooms is the main event and takes the biggest block of time; the other stops are built around it. It finishes at Black Watch Pub — a short, low-effort stop you can skip if you're ready to call it. Best suited to couples, friends, adults, and solo who want a planned Upland outing without improvising between stops.

The story

The itinerary

3 stops, one great day

1
1h 30m
Experience Machine Escape Rooms
Family
What to do — Book your escape room session in advance for the evening. Arrive 15 minutes early for instructions and to get into character.
Scout Side Quest
Assign each other secret operative codenames before going in. You have to use them every time you need help.
2.4 mi · 8 min drive
Then A short drive or ride will take you to your dinner destination.
2
1h 30m
Allegro
Food & Drink
Pizza, pasta & other classic Italian meals are the draw at this charming establishment with a patio.
What to do — Enjoy a romantic dinner on the patio if available, choosing from a menu of traditional Italian favorites. Consider a glass of wine to complement your meal.
Scout Side Quest
Try to guess each other’s exact dinner order before opening the menu. Winner gets dibs on the first bite.
2.4 mi · 8 min drive
Then Take a short walk to a nearby pub for an optional nightcap.
3
Optional 1h 30m
Black Watch Pub
Nightlife
Laid-back British bar offering pub grub, brews & weekly live bands in a casual atmosphere.
What to do — Optional nightcap for those who drink — skip it and the plan still works. Enjoy a drink and chat in the relaxed atmosphere of the pub.

Scout Stories

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The route

On the map

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Common questions

Planning this outing

Is this a good Upland itinerary for couples?: Yes. It's built for couples, friends, adults, and solo and runs about 4 hr 30 min across 3 stops, starting at Experience Machine Escape Rooms.
How long does this outing take?: Plan on 4 hr 30 min door to door, including time between stops.
How much does this Upland itinerary cost?: Roughly $100–$250 per person, before parking and tips. Free and low-cost stops are marked on each card.
Is this itinerary walkable?: Not entirely. The stops cover about 4.8 miles, so you'll drive or rideshare between at least one pair.
Do I need reservations?: No. Every stop on this plan takes walk-ins, though weekends move faster if you arrive early.

Keep exploring

Different moods, same city.

See all things to do in Upland →

Arts & Culture
Upland
Upland Historic Downtown & Budget Eats
Spend a leisurely afternoon exploring the charm of Historic Downtown Upland, soaking in the local architecture and atmosphere. Follow it up with a budget-friendly and satisfying lunch at The Hat, famous for its pastrami. Conclude your outing by browsing for unique treasures at DeeLux in nearby Claremont, offering a curated selection of second-hand clothing.
Duration
3 hrs
Cost
$15–$30
Ideal for
Solo · Friends
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